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404-86-4 Usage

Description

Capsaicin is the main chemical responsible for the pungent taste and burning sensation in chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and is a naturally occurring substance considered a biochemical pesticide by the U.S. Environmental Protection Agency. Capsaicin is a hydrophobic, colorless, odorless, crystalline to waxy compound and is the primary component of capsaicinoids, which are produced as a secondary metabolite by chili peppers, likely as a deterrent against herbivores.

Uses

Used in Food Industry:
Capsaicin is used as a flavor enhancer for sauces where a pungent note is desired, providing the characteristic heat and spiciness to various dishes.
Used in Pharmaceutical Industry:
Capsaicin is used as a topical analgesic for relieving pain from arthritis, muscle aches, and sprains. It acts as a rubefacient, dilating blood vessels and causing a localized numbing sensation by overwhelming nerves with its heat effect.
Used in Neurobiological Research:
Capsaicin is employed as a tool in neurobiological research, acting as a prototype vanilloid receptor agonist. It is used to study the physiology of pain and the effects as a counterirritant and gastrointestinal stimulant.
Used in Pain Management:
Capsaicin is used in many topical ointments to relieve the pain of peripheral neuropathy, specifically targeting pain in the nerve endings near the surface of the skin.
Used in Multiple Sclerosis Therapy:
Capsaicin is utilized as a K channel blocker in the treatment of multiple sclerosis, potentially providing therapeutic benefits for patients with this condition.
Used in Animal Repellent Industry:
As an animal repellent, capsaicin is used against insects and mites, and has been registered for use in the United States since 1962.
Used in Self-Defense:
Capsaicin is also used in pepper spray, serving as a self-defense tool due to its irritating effects on the eyes and respiratory system.

History

Capsaicin is a naturally occurring substance that is responsible for the burning, pungent sensation associated with the ingestion of hot peppers from the Capsicum genus. The effect elicited by these peppers is at the origin of the name Capsicum, which derives from the Greek kapto, meaning “to bite”. Hot peppers are a native plant from the American tropics and their use can be traced back to the Aztec and Inca civilizations. The Aztecs named them “chilies” and used them for culinary purposes. After discovery of the New World, chili pods were introduced in Europe and their cultivation expanded to other parts of the globe. Nowadays, hot peppers are found in nearly every country and are an important part of the culinary tradition of many different cultures. The active component of chili peppers was initially isolated by J. C. Thresh in 1846. The compound was named “capsaicin” and its chemical structure was later determined by E. K. Nelson in 1919. The complete chemical synthesis of 8-methyl-N- vanillyl-6-nonenamide (capsaicin’s IUPAC* name) was reported in 1930 by Spath &Darling. In the 1960’s, Japanese investigators identified additional substances from Capsicum extracts with similar chemical and pharmacological properties that were termed “capsaicinoids”. Currently, this family of chemical analogues includes both natural (homodihydrocapsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin and capsaicin) and synthetic (nonivamide) members.

History

In 1816, Christian Friedrich Bucholz (1770–1818) first carried out the purification of capsaicin. He obtained incompletely purified capsaicin and named it “capsaicin” . In 1876, John Clough Thresh (1850–1932) further purified and got pure capsaicin and named it capsaicin. In 1919, Nelson identified the capsaicin structure. In 1930, E.?Spath and S.?F. Darling used chemical synthesis method for the first time to successfully synthesize capsaicin. In 1961, the Japanese chemists S.? Kosuge and Y.? Inagaki isolated similar substances from capsicum and named them capsaicinoids. More than 14 capsaicin homologues have been found till now, the structures are similar with capsaicin, and the typical structure is H3CO(HO)-C6H3-CH2-NHCO-R, which is only different from R group. Capsaicin is the highest content in chili pepper. Capsaicin and dihydrocapsaicin are the most potent active substances in capsicum. Capsaicin and its analogues have been synthesized in large quantities in practice and can be used not only in medicine but also in agriculture and industry. Although there is a long history of pharmacological and chemical studies on capsaicin, until November 16, 2009, the US Food and Drug Administration (FDA) approved the first containing high concentration capsaicin prescription Qutenza (8% capsaicin) patch for the treatment of postherpetic neuralgia. At present, most countries have capsaicin prescription drugs on market, but clinical indications are limited in the treatment of pain.

Application in Particular Diseases

In Osteoarthritis: Capsaicin, an extract of red peppers that causes release and ultimately depletion of substance P from nerve fibers, has been beneficial in providing pain relief in OA when applied topically over affected joints. It may be used alone or in combination with oral analgesics or NSAIDs. To be effective, capsaicin must be used regularly, and it may take up to 2 weeks to work. It is well tolerated, but some patients experience temporary burning or stinging at the site of application. Patients should be warned not to get the cream in their eyes or mouth and to wash their hands after application. Application of the cream, gel, or lotion is recommended four times daily, but tapering to twice-daily application may enhance long-term adherence with adequate pain relief.

Indications

Capsaicin (Zostrix) is approved for the relief of pain following herpes zoster infection (postherpetic neuralgia). The drug depletes neurons of substance P, an endogenous neuropeptide that may mediate cutaneous pain. It is applied to affected skin after open lesions have healed. Local irritation is common.

Biological Activity

Prototypic vanilloid receptor agonist (pEC 50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptive and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset? .

Biochem/physiol Actions

Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.

Pharmacology

Hbgyes, A. (1878) first reported that capsaicin has a strong stimulating effect, which is the first pharmacological study on capsaicin. And then, a serial of pharmacological effects were discovered. The discovery of capsaicin receptor further explains the mechanism of capsaicin. The capsaicin receptor, also known as transient voltage receptor cation channel V1 (TRPV1), is a nonselective ligand-gated cation channel. TRPV1 is widely distributed in the body, mainly in sensory neurons, and can also be activated by heat and friction damage. Studies on the analgesic effect of capsaicin were carried out earlier and more thoroughly. Capsaicin can act on sensory nerve C primary afferent fibers, bind the end of the neuronal TRPV1 receptor. Capsaicin (1?μM) can result in inward calcium influx, cell depolarization, neuronal excitation, and glutamate release. The sustained neuron excitement and then failure can result in analgesic and antipruritic effects. The mutation of the capsaicin receptor can not only induce obesity but also may be associated with the occurrence of diabetes. Capsaicin can activate and recruit brown fat to prevent obesity. Brown fat can produce non-shivering heat in cold environment and participate in energy consumption. A 10–130?mg daily capsaicin can significantly increase the body’s energy and fat consumption. Capsaicin also has a protective effect on the cardiovascular system. Treatment of capsaicin with rats at a dose of 15?mg/kg can not only promote animal blood circulation and strengthen the cardiovascular function but also reduce the blood pressure , the serum cholesterol, and triglyceride levels. The study result of capsaicin on tumor is still controversial. The epidemiology and basic research have suggested that capsaicin can not only be used as a carcino400 gen but also can prevent cancer. It has been shown that capsaicin can induce cancer cell apoptosis, and animal experiments have shown that prolonged use of capsaicin on the skin can induce skin cancer. Capsaicin is able to scavenge free radicals and inhibit oxidative stress. Capsaicin can promote gastric secretion, increase appetite, relieve flatulence, improve digestive function, and also prevent gastrointestinal infection and diarrhea. Capsaicin can improve the performance of sports and anti-fatigue. Capsaicin is capable of thinning lung mucus, in favor of sputum discharging, enhancing lung tissue perfusion, and preventing and treating emphysema. Capsaicin is also beneficial on psoriasis, frostbite, cold, etc. In addition, capsaicin is also used for the paralysis of peripheral nerve function for hypertension treatment. Capsaicin can be absorbed by the intestine and skin and is able to pass through the blood-brain barrier.

Anticancer Research

Capsaicin is the major pungent ingredient in red and green chili pepper. It is reportedto induce apoptosis selectively in cancer cells and can suppress the activation ofNF-κB through suppression of NF-κB inhibitor IκBα (Aggarwal and Shishodia 2004). It shows anticancer effects in animal models and suppresses carcinogenesisin colon, skin, lung, tongue, and prostate cancers by altering the metabolism ofcarcinogens. It selectively suppresses the human cancer cell growth of prostate,leukemic, glioma, gastric, and hepatic cancers. It inhibited the tumorigenesis linkedand IL-6-induced activation of STAT-3 and STAT3-regulated gene products likecyclin D1, Bcl-2, Bcl-xL, survivin, and VGEF. It arrests cells in G1 phase andinduces apoptosis (Aggarwal et al. 2008; Clark and Lee 2016).

Clinical Use

In clinical practice, capsaicin is mainly used for topical administration, such as in the treatment of osteoarthritis and rheumatoid arthritis pain, diabetic nerve pain, pain after surgery, chemotherapy- or radiotherapy-induced oral pain, psoriasis, etc. Capsaicin irritates the mucous membrane to cause sneezing, nose bleeding, coughing, mucus secretion, tears, bronchoconstriction, breathing difficulties, and other symptoms. The main adverse effects of capsaicin preparations are contact dermatitis, skin inflammation or blisters, and in severe situation burn-like lesion.

Synthesis

From 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation from cis-capsaicin, pelargonic acid vanillamide and dihydrocapsaicin; reaction of capsaicin

Potential Exposure

Botanical animal and insect repellent used to repel birds, voles, deer, rabbits, squirrels, insects, and attacking dogs. Capsaicin, which is made from the Capsicum red chili pepper can be used indoors to protect carpets and upholstered furniture, and outdoors to protect fruit and vegetable crops, flowers, ornamental plants, shrubbery, trees, and lawns. It is also used in pepper sprays such as MACE, and as an analgesic in creams, lotions and solid sticks to reduce arthritic, postoperative and neuopathic pain, such as shingles. Capsaicin is obtained by grinding dried, ripe Capsicum frutescens L. chili peppers into a fine powder. The oleoresin is derived by distilling the powder in a solvent and evaporating the solvent. The resulting highly concentrated liquid has little odor but has an extremely pungent taste

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Recrystallise capcaicin from pet ether (b 40-60o), or pet ether/Et2O (9:1). Also purify it by chromatography on neutral Al2O3 (grade V) and elute successively with *C6H6, *C6H6/EtOAc (17:3) then *C6H6/EtOAc (7:3), and distil it at 120o/10-5mm, then repeatedly recrystallise the needles from isopropanol (charcoal). [Crombie et al. J Chem Soc 11025 1955, Bennett & Kirby J Chem Soc(C) 442 1968.] It causes pain and is neurotoxic [Bevan & Szolcsanyi Trends in Pharmacol Sci 11 330 1990, Beilstein 13 IV 2588].

Incompatibilities

Slowly hydrolyzes in water, releasing ammonia and forming acetate salts.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Noncombustible containers should be crushed and buried under more than 40 cm of soil. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office

References

1) Gunthorpe et al. (2002) The diversity in the vanilloid (TRPV) receptor family of ion channels; Trends Pharmacol. Sci. 23 183 2) Van Der Stelt and Di Marzo (2004) Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels; Eur. J. Biochem. 271 1827 3) Perkins and Campbell (1992) Capsazepine reversal of the antinociceptive action of capsaicin in vivo; Br. J. Pharmacol. 107 329 4) Kim et al..(2003) Capsaicin exhibits anti-inflammatory property by inhibiting IkB-a degradation in LPS-stimulated peritoneal macrophages; Cell. Signal., 15 299 5) Di Marzo et al. (2001) Hypolocomotor effects in rats of capsaicin and two long chain capsaicin homologues; Eur. J. Pharmacol., 420 123

Check Digit Verification of cas no

The CAS Registry Mumber 404-86-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,0 and 4 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 404-86:
(5*4)+(4*0)+(3*4)+(2*8)+(1*6)=54
54 % 10 = 4
So 404-86-4 is a valid CAS Registry Number.
InChI:InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

404-86-4 Well-known Company Product Price

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  • TCI America

  • (M1149)  Capsaicin (Natural)  >60.0%(HPLC)

  • 404-86-4

  • 1g

  • 965.00CNY

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  • Sigma-Aldrich

  • (12084)  Capsaicin  analytical standard

  • 404-86-4

  • 12084-50MG-F

  • 2,039.31CNY

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404-86-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name capsaicin

1.2 Other means of identification

Product number -
Other names (E)-Capsaicin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:404-86-4 SDS

404-86-4Synthetic route

Vanillylamin
1196-92-5

Vanillylamin

(E)-8-Methylnon-6-enoic acid chloride
95636-02-5

(E)-8-Methylnon-6-enoic acid chloride

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Stage #1: Vanillylamin With sodium hydrogencarbonate In chloroform; water at 20℃; for 0.75h;
Stage #2: (E)-8-Methylnon-6-enoic acid chloride In chloroform; water at 20 - 40℃; for 1h;
91%
In diethyl ether for 72h; Ambient temperature;
In diethyl ether 1.) RT, 2 h, 2.) reflux, 2 h; Yield given;
trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

vanillylamine hydrochloride
7149-10-2

vanillylamine hydrochloride

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Schlenk technique;75%
trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With thionyl chloride Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether;
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / Heating
2: diethyl ether / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / Heating
2: diethyl ether
View Scheme
(E)-N-[(4β-D-glucopyranosyloxy)-3-methoxyphenylmethyl]-8-methylnon-6-enamide

(E)-N-[(4β-D-glucopyranosyloxy)-3-methoxyphenylmethyl]-8-methylnon-6-enamide

A

D-Glucose
2280-44-6

D-Glucose

B

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
at 37℃; for 16h; β-glucosidase; enzymatic hydrolysis of capsaicin glucoside with α- or β-glucosidase;
(E)-1-hydroxy-6-methylhept-4-ene
59721-82-3

(E)-1-hydroxy-6-methylhept-4-ene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h
2: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
3: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
4: 92 percent / aq. NaOH / methanol / 15 h / Heating
5: SOCl2 / 2 h / Heating
6: diethyl ether / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: pyridine; phosphorus (III)-bromide
2: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
3: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester
179617-41-5

Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
2: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
3: 92 percent / aq. NaOH / methanol / 15 h / Heating
4: SOCl2 / 2 h / Heating
5: diethyl ether / 2 h / Heating
View Scheme
(E)-methyl 8-methyl-6-nonenoate
112375-54-9

(E)-methyl 8-methyl-6-nonenoate

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / aq. NaOH / methanol / 15 h / Heating
2: SOCl2 / 2 h / Heating
3: diethyl ether / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: aq. KOH / ethanol / 1 h / Heating
2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
3: diethyl ether / 72 h / Ambient temperature
View Scheme
trans-6-methyl-hept-4-enoic acid ethyl ester
179617-47-1

trans-6-methyl-hept-4-enoic acid ethyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature
2: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h
3: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
4: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
5: 92 percent / aq. NaOH / methanol / 15 h / Heating
6: SOCl2 / 2 h / Heating
7: diethyl ether / 2 h / Heating
View Scheme
2-((E)-6-Methyl-hept-4-enyl)-malonic acid dimethyl ester
179617-42-6

2-((E)-6-Methyl-hept-4-enyl)-malonic acid dimethyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
2: 92 percent / aq. NaOH / methanol / 15 h / Heating
3: SOCl2 / 2 h / Heating
4: diethyl ether / 2 h / Heating
View Scheme
6-hydroxyhexanal lactol
93545-84-7

6-hydroxyhexanal lactol

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: KOtBu / dimethylformamide / Ambient temperature
2: HNO3, NaNO2 / 1 h / 75 °C
3: 78 percent / CrO3 / acetone
4: SOCl2 / 2 h / Heating
5: diethyl ether
View Scheme
(Z)-1-hydroxy-8-methylnon-6-ene
90369-18-9

(Z)-1-hydroxy-8-methylnon-6-ene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HNO3, NaNO2 / 1 h / 75 °C
2: 78 percent / CrO3 / acetone
3: SOCl2 / 2 h / Heating
4: diethyl ether
View Scheme
(E)-1-hydroxy-8-methylnon-6-ene
90369-20-3

(E)-1-hydroxy-8-methylnon-6-ene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / CrO3 / acetone
2: SOCl2 / 2 h / Heating
3: diethyl ether
View Scheme
(5-carboxypentyl)triphenylphosphonium bromide
50889-29-7

(5-carboxypentyl)triphenylphosphonium bromide

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: t-BuOK / dimethylformamide / 15 h / Ambient temperature
2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h
3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 4 steps
1: t-BuOK / dimethylformamide / 15 h / Ambient temperature
2: 2M NaNO2, 5M aq. HNO3 / 0.5 h / 70 - 75 °C
3: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h
4: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0 °C
1.2: 12 h / 0 - 20 °C
2.1: sodium nitrite; nitric acid / water / 0.58 h / 75 °C
3.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique
View Scheme
vanillin
121-33-5

vanillin

KOH-solution

KOH-solution

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate / 3 h / 180 °C
2: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
(6Z)-8-methyl-6-nonaneneoic acid
31467-60-4

(6Z)-8-methyl-6-nonaneneoic acid

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2M NaNO2, 5M aq. HNO3 / 0.5 h / 70 - 75 °C
2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h
3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 2 steps
1: sodium nitrite; nitric acid / water / 0.58 h / 75 °C
2: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique
View Scheme
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: conc. H2SO4 / Heating
2: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature
4: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
5: aq. KOH / ethanol / 1 h / Heating
6: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
7: diethyl ether / 72 h / Ambient temperature
View Scheme
methyl 6-oxohexanoate
6654-36-0

methyl 6-oxohexanoate

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
3: aq. KOH / ethanol / 1 h / Heating
4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
5: diethyl ether / 72 h / Ambient temperature
View Scheme
methyl 6-hydroxycaproate
4547-43-7

methyl 6-hydroxycaproate

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature
3: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
4: aq. KOH / ethanol / 1 h / Heating
5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
6: diethyl ether / 72 h / Ambient temperature
View Scheme
Benzoic acid 1-(1-benzenesulfonyl-2-methyl-propyl)-5-methoxycarbonyl-pentyl ester

Benzoic acid 1-(1-benzenesulfonyl-2-methyl-propyl)-5-methoxycarbonyl-pentyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
2: aq. KOH / ethanol / 1 h / Heating
3: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
4: diethyl ether / 72 h / Ambient temperature
View Scheme
2,3-dichlorotetrahydro-2H-pyran
5631-95-8

2,3-dichlorotetrahydro-2H-pyran

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: diethyl ether
2: sodium; diisopropyl ether
3: pyridine; phosphorus (III)-bromide
4: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
5: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
3-chloro-2-isopropyltetrahydropyran
59721-81-2

3-chloro-2-isopropyltetrahydropyran

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium; diisopropyl ether
2: pyridine; phosphorus (III)-bromide
3: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
4: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
(E)-7-bromo-2-methyl-3-heptene
59721-83-4

(E)-7-bromo-2-methyl-3-heptene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
2: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
C44H75NO12P(1-)*Na(1+)

C44H75NO12P(1-)*Na(1+)

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; secretory phospholipase A2 from venom of Agkistrodon piscivorus piscivorus; potassium chloride; calcium chloride at 50℃; pH=7.5; aq. buffer;
N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxycarbonyl]dopamine
1221557-61-4

N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxycarbonyl]dopamine

A

capsaicin
404-86-4

capsaicin

B

6-bnromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one
223420-41-5

6-bnromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one

Conditions
ConditionsYield
With water Photolysis;
(E)-[8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl 2-methoxy-4-[(8-methylnon-6-enamido)methyl]phenyl carbonate
1221557-70-5

(E)-[8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl 2-methoxy-4-[(8-methylnon-6-enamido)methyl]phenyl carbonate

A

8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxy-4-(hydroxymethyl)coumarin
1221557-66-9

8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxy-4-(hydroxymethyl)coumarin

B

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With water Photolysis;
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
3.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 3 steps
1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1.1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2.1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
3.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
4.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
4.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
3: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
4: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
Vanillylamin
1196-92-5

Vanillylamin

trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With lipase In tert-Amyl alcohol at 45℃; for 48h; Molecular sieve; Enzymatic reaction;
4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone
61152-59-8

4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
2.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
vanillin
121-33-5

vanillin

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
2.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1.1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
2.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
3.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 3 steps
1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
capsaicin
404-86-4

capsaicin

butyryl chloride
141-75-3

butyryl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl butanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl butanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;96%
With triethylamine In dichloromethane at 20℃; for 13 - 21h; dark; Heating / reflux;95%
With triethylamine In dichloromethane at 20 - 45℃; for 24 - 32h; Heating / reflux;95%
With triethylamine In dichloromethane at 20℃; Reflux;95%
capsaicin
404-86-4

capsaicin

Stearoyl chloride
112-76-5

Stearoyl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl octadecanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl octadecanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;96%
capsaicin
404-86-4

capsaicin

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

capsaicin palmitate

capsaicin palmitate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 40℃; Darkness; Reflux; Large scale;95%
With triethylamine; dmap In dichloromethane at 20℃; for 13 - 21h; Heating / reflux;95%
capsaicin
404-86-4

capsaicin

propionyl chloride
79-03-8

propionyl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl propanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl propanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;94%
capsaicin
404-86-4

capsaicin

N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride

N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-(4-methoxybenzyl)benzene sulfonimidate

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-(4-methoxybenzyl)benzene sulfonimidate

Conditions
ConditionsYield
Stage #1: capsaicin With 1H-imidazole In dichloromethane at 20℃; for 0.0833333h;
Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 5h;
Stage #3: N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 60℃; for 10h; Sealed tube; Inert atmosphere;
94%
capsaicin
404-86-4

capsaicin

dihydrocapsaicin
19408-84-5

dihydrocapsaicin

Conditions
ConditionsYield
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 12h; Reagent/catalyst; Green chemistry; chemoselective reaction;93%
With platinum (IV) oxide hydrate; hydrogen In methanol at 20℃; under 760.051 Torr; for 7h; Solvent;85%
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;
capsaicin
404-86-4

capsaicin

pivaloyl chloride
3282-30-2

pivaloyl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl 2,2-dimethylpropanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl 2,2-dimethylpropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;92.5%
capsaicin
404-86-4

capsaicin

4-bromomethylphenylboronic acid pinacol ester
138500-85-3

4-bromomethylphenylboronic acid pinacol ester

C31H44BNO5

C31H44BNO5

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 2h;90.5%
capsaicin
404-86-4

capsaicin

chloroacetyl chloride
79-04-9

chloroacetyl chloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-chloroacetate
1236876-87-1

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-chloroacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;90.3%
(1R,2S,5R)-menthyl chloroformate
14602-86-9

(1R,2S,5R)-menthyl chloroformate

capsaicin
404-86-4

capsaicin

(1S,2S,5R)-5-methyl-2-(methylethyl)cyclohexyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenoxy}formate
913290-19-4

(1S,2S,5R)-5-methyl-2-(methylethyl)cyclohexyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenoxy}formate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;87%
capsaicin
404-86-4

capsaicin

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methoxyphenoxy}formate
913290-18-3

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methoxyphenoxy}formate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;86.5%
capsaicin
404-86-4

capsaicin

acetyl chloride
75-36-5

acetyl chloride

O-acetylcapsaicin

O-acetylcapsaicin

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;86%
capsaicin
404-86-4

capsaicin

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

C25H30N2O3

C25H30N2O3

Conditions
ConditionsYield
Stage #1: capsaicin With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique;
83%
dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

capsaicin
404-86-4

capsaicin

(E)-N-(3-methoxy-4-(4-nitrophenoxy)benzyl)-8-methylnon-6-enamide

(E)-N-(3-methoxy-4-(4-nitrophenoxy)benzyl)-8-methylnon-6-enamide

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Schlenk technique;83%
formic acid
64-18-6

formic acid

capsaicin
404-86-4

capsaicin

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl formate
913290-13-8

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl formate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h;80.2%
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

capsaicin
404-86-4

capsaicin

C23H35NO3

C23H35NO3

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene for 1.5h; Inert atmosphere; Reflux;79%
1-(prop-1-yn-1-yl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one

1-(prop-1-yn-1-yl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one

capsaicin
404-86-4

capsaicin

C28H34INO5

C28H34INO5

Conditions
ConditionsYield
With caesium carbonate In ethanol at 20℃; chemoselective reaction;77%
capsaicin
404-86-4

capsaicin

methyl chloroacetate
96-34-4

methyl chloroacetate

{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-acetic acid methyl ester

{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-acetic acid methyl ester

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium carbonate; sodium iodide In acetone for 6h; Heating / reflux;71.4%
With disodium hydrogenphosphate; potassium carbonate; sodium iodide In acetone for 6h; Heating / reflux;71.4%
capsaicin
404-86-4

capsaicin

N-ethylmethylalanine

N-ethylmethylalanine

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylalanine hydrochloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylalanine hydrochloride

Conditions
ConditionsYield
Stage #1: capsaicin; N-ethylmethylalanine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
70.2%
capsaicin
404-86-4

capsaicin

1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride
58685-78-2

1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride

C28H38N2O4*ClH

C28H38N2O4*ClH

Conditions
ConditionsYield
Stage #1: capsaicin; 1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
68.2%
capsaicin
404-86-4

capsaicin

2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride

2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride

C31H49N3O4*ClH

C31H49N3O4*ClH

Conditions
ConditionsYield
Stage #1: capsaicin; 2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
63.2%
capsaicin
404-86-4

capsaicin

N,N-diethyl-L-isoleucine

N,N-diethyl-L-isoleucine

C28H46N2O4*ClH

C28H46N2O4*ClH

Conditions
ConditionsYield
Stage #1: capsaicin; N,N-diethyl-L-isoleucine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
60.5%
BOC-glycine
4530-20-5

BOC-glycine

capsaicin
404-86-4

capsaicin

C25H38N2O6

C25H38N2O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;60.5%
N-ethyl-N-methyl-glycine

N-ethyl-N-methyl-glycine

capsaicin
404-86-4

capsaicin

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylglycine hydrochloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylglycine hydrochloride

Conditions
ConditionsYield
Stage #1: N-ethyl-N-methyl-glycine; capsaicin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
60.1%
capsaicin
404-86-4

capsaicin

N,N'-(3,3'-Bi-4-hydroxy-5-methoxybenzyl)di-8-methylnon-(E)-6-enamide
134386-10-0

N,N'-(3,3'-Bi-4-hydroxy-5-methoxybenzyl)di-8-methylnon-(E)-6-enamide

Conditions
ConditionsYield
With riboflavin In ethanol at 30℃; for 0.333333h; Irradiation; pH 5.0 (citrate buffer);60%
With Capsicum annuum var. annuum cell protein extract; dihydrogen peroxide In water at 30℃; for 1.25h; pH=7.0;
With dihydrogen peroxide; horseradish peroxidase In aq. buffer at 20℃; for 0.166667h; pH=5.5;
capsaicin
404-86-4

capsaicin

N-ethyl-N-isopropylglycine

N-ethyl-N-isopropylglycine

(E)-2-methoxy-4-((8-methylnon-6-enoylamino)methyl)phenyl N-ethyl-N-isopropylglycine hydrochloride

(E)-2-methoxy-4-((8-methylnon-6-enoylamino)methyl)phenyl N-ethyl-N-isopropylglycine hydrochloride

Conditions
ConditionsYield
Stage #1: capsaicin; N-ethyl-N-isopropylglycine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
59.3%
capsaicin
404-86-4

capsaicin

4-carbamothioylbenzoic acid
4989-36-0

4-carbamothioylbenzoic acid

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 4-carbamothioyl benzoate

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 4-carbamothioyl benzoate

Conditions
ConditionsYield
Stage #1: capsaicin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.333333h;
Stage #2: 4-thiocarbamoylbenzoic acid In dichloromethane
57.3%
ketoprofen
22071-15-4

ketoprofen

capsaicin
404-86-4

capsaicin

2-(3-benzoyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnon-6-enoylamino)-methyl]-phenyl ester
1224428-97-0

2-(3-benzoyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnon-6-enoylamino)-methyl]-phenyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30 - 35℃;56.6%

404-86-4Relevant articles and documents

A convenient transformation of 2-alkylidenecycloalkanones into alkyl-substituted bicyclo[ n.1.0]alkan-1-ols: Application to the synthesis of capsaicin

Kananovich, Dzmitry G.,Zubrytski, Dzmitry M.,Kulinkovich, Oleg G.

, p. 1043 - 1046 (2010)

Treatment of 2-alkylidenecycloalkanones with hydrogen iodide in benzene and subsequent reaction of the obtained -iodo ketones with zinc dust in THF in the presence of chlorotrimethylsilane or titanium(IV) chlorotriisopropoxide led to exo- and endo-(n+3)-alkylbicyclo[n.1.0]alkan-1-ols in high yields. Cyclization of the intermediate -iodo ketones under these conditions proceeded in a moderate to good diastereoselectivity, and the resulted bicyclic cyclopropanols were easily separated by column chromatography over silica gel. exo-7- Isopropylbicyclo[4.1.0]heptan-1-ol obtained in this manner was efficiently employed as a key intermediate in the synthesis of capsaicin. Georg Thieme Verlag Stuttgart - New York.

Aliphatic hydroxylation and epoxidation of capsaicin by cytochrome P450 CYP505X

Migglautsch, Anna K.,Willim, Melissa,Schweda, Bettina,Glieder, Anton,Breinbauer, Rolf,Winkler, Margit

, p. 6199 - 6204 (2018/09/21)

Microbial cytochrome P450 enzymes (CYPs) are able to mimic the metabolism of human CYPs. One challenge is to identify the respective drug metabolites and to compare substrate specificities to those of the human enzymes. In this study, a class VIII self-sufficient CYP from Aspergillus fumigatus (CYP505X) and variants of this enzyme were heterologously expressed in E. coli. The substrate scope of the variants was determined using active pharmaceutical ingredients (APIs) and (hetero)cyclic compounds. Capsaicin – the active compound in chili peppers – was oxidized most efficiently (4.36 μM/min) in a whole cell mediated biotransformation. The products were isolated, purified and their structures elucidated by 1D and 2D NMR. The two major metabolites showed modifications on the lipophilic side chain. Specifically, capsaicin was hydroxylated at position 8 to give (E)-8-hydroxy-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide and epoxidized at the double bond to give N-(4-hydroxy-3-methoxybenzyl)-5-(3-isopropyloxiran-2-yl)-pentanamide.

[8-[Bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl Moieties as photoremovable protecting groups for compounds with COOH, NH 2, OH, and C-O functions

Hagen, Volker,Kilic, Funda,Schaal, Janina,Dekowski, Brigitte,Schmidt, Reinhard,Kotzur, Nico

scheme or table, p. 2790 - 2797 (2010/08/03)

We introduce a variant of coumarin-based photoactivatable protecting groups and use it exemplarily for caging of a carboxylic acid, an amine, a phenol, and a carbonyl compound. The caged compounds are efficiently photolyzed at long-wavelength UV/vis irradiation. Compared to the corresponding (6-bromo-7-hydroxycoumarin-4-yl)methyl (Bhc) derivatives, the novel coumarin-type caged compounds are distinguished by (i) dramatically increased solubilities in aqueous buffers, (ii) lower pKa values of the C7 hydroxyl of the coumarin chromophore, thus permitting efficient photorelease at lower pH, and (iii) higher photolysis quantum yields in the case of photoprotected carbonyl compounds. The primary step of the photocleavages occurs with rate constants of about 109 s-1.

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