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3690-05-9

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3690-05-9 Usage

Uses

p-Coumaryl Alcohol is a monolignon which is used to synthesize lignin through a biosynthetic enzyme-catalyzed phenol dehydrogenation reaction.

Definition

ChEBI: A primary alcohol being cinnamyl alcohol hydroxylated at C-4 of the phenyl ring.

Check Digit Verification of cas no

The CAS Registry Mumber 3690-05-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,9 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 3690-05:
(6*3)+(5*6)+(4*9)+(3*0)+(2*0)+(1*5)=89
89 % 10 = 9
So 3690-05-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2

3690-05-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-hydroxycinnamyl alcohol

1.2 Other means of identification

Product number -
Other names p-coumaryl alcohol

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:3690-05-9 SDS

3690-05-9Synthetic route

methyl 4-hydroxycinnamate
3943-97-3

methyl 4-hydroxycinnamate

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 6h;96%
1-hydroxy-3-(4-acetoxyphenyl)-2-propen
1202495-53-1

1-hydroxy-3-(4-acetoxyphenyl)-2-propen

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With β‐cyclodextrin In water; acetone at 60℃; for 6h; Green chemistry;95%
C14H18O3

C14H18O3

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With β‐cyclodextrin In water; acetone at 60℃; for 6h; Green chemistry;93%
methyl p-hydroxycinnamate
3943-97-3, 19367-38-5, 61240-27-5

methyl p-hydroxycinnamate

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 0℃; for 1.5h;90%
With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 0.5h; Inert atmosphere;62%
C11H14O3

C11H14O3

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With β‐cyclodextrin In water; acetone at 60℃; for 6h; Green chemistry;87%
4-hydroxybenzenediazonium tetrafluoroborate

4-hydroxybenzenediazonium tetrafluoroborate

allyl alcohol
107-18-6

allyl alcohol

A

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

B

dihydro-p-coumaryl aldehyde
20238-83-9

dihydro-p-coumaryl aldehyde

Conditions
ConditionsYield
With sodium acetate; palladium diacetate In methanol at 0℃; for 6h; Heck Reaction;A 72%
B 11%
C16H16O4S

C16H16O4S

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With β‐cyclodextrin In water; acetone at 60℃; for 5h; Green chemistry;59%
ethyl 3-(4-hydroxyphenyl)prop-2-enoate
7361-92-4, 7362-39-2, 2979-06-8

ethyl 3-(4-hydroxyphenyl)prop-2-enoate

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 18h; Reduction;
With diisobutylaluminium hydride In toluene at -78 - 25℃; for 3.75h; Inert atmosphere;
p-hydroxy-cinnamaldehyde
20711-53-9, 88264-59-9, 2538-87-6

p-hydroxy-cinnamaldehyde

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With β-nicotinamide adenine dinucleotide 2’-phosphate reduced tetrasodium salt; Arabidopsis thaliana cinnamyl alcohol dehydrogenase 5 at 30℃; Kinetics; Enzymatic reaction;
Stage #1: p-hydroxy-cinnamaldehyde With 1,4-dithio-L-threitol; NADPH at 30℃; for 0.5h; Enzymatic reaction;
Stage #2: With acetic acid In methanol pH=7.5; Kinetics;
4-acetaminophenol
103-90-2

4-acetaminophenol

A

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

B

dihydro-p-coumaryl aldehyde
20238-83-9

dihydro-p-coumaryl aldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrafluoroboric acid / isopropyl alcohol / 3 h / 90 °C
1.2: 0 °C
2.1: sodium acetate; palladium diacetate / methanol / 6 h / 0 °C
View Scheme
4-(4'-hydroxyphenyl)but-3-en-2-one
22214-30-8, 59417-71-9, 3160-35-8

4-(4'-hydroxyphenyl)but-3-en-2-one

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 4 h / Reflux
2: lithium aluminium tetrahydride / chlorobenzene; tetrahydrofuran / 4 h / 20 °C
View Scheme
ethyl (E)-4-hydroxycinnamate
2979-06-8, 7361-92-4, 7362-39-2

ethyl (E)-4-hydroxycinnamate

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene at 20℃; for 4h;
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine; piperidine / 90 - 105 °C
2: triethylamine / tetrahydrofuran / 0.5 h / -7 °C
3: sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 10 °C
View Scheme
para-coumaric acid
7400-08-0

para-coumaric acid

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 0.5 h / -7 °C
2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 10 °C
View Scheme
Multi-step reaction with 2 steps
1: 45 h / Irradiation; Reflux
2: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 1.5 h / 0 °C
View Scheme
C12H12O5

C12H12O5

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 10℃; for 2h;
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

Conditions
ConditionsYield
With Escherichia coli BL21-Gold(DE3) lacIQ1 pALXtreme-tal-4cl-ccr-cad at 25℃; for 17h; Enzymatic reaction;
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

3-(4-hydroxyphenyl)propan-1-ol
10210-17-0

3-(4-hydroxyphenyl)propan-1-ol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12h;98%
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

p-hydroxy-cinnamaldehyde
20711-53-9, 88264-59-9, 2538-87-6

p-hydroxy-cinnamaldehyde

Conditions
ConditionsYield
With MoO2Cl2(DMSO)2; dimethyl sulfoxide for 0.166667h; Swern Oxidation; Microwave irradiation;97%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 20℃; for 0.5h;81%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 0.5h; Inert atmosphere;43%
tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate

tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

[(C5(CH3)5)Ru(η6-p-coumaryl alcohol)]PF6
1160168-69-3

[(C5(CH3)5)Ru(η6-p-coumaryl alcohol)]PF6

Conditions
ConditionsYield
In dichloromethane byproducts: CH3CN; (Ar, Schlenk technique); addn. of phenol deriv. to CH2Cl2 soln. of ruthenium compd., stirring for several hs at room temp.; concg., addn. of ether, filtration, washing with ether and hexane, elem.anal.;83%
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

3-(3-hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1 -one
35400-60-3

3-(3-hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1 -one

(E)-3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxy-3-(3-(4-hydroxyphenyl)allyl)phenyl)propan-1-one

(E)-3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxy-3-(3-(4-hydroxyphenyl)allyl)phenyl)propan-1-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile at 20℃; for 3h; Inert atmosphere;69%
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

herbacetin
527-95-7

herbacetin

demethoxyrhodiolin
134070-57-8

demethoxyrhodiolin

Conditions
ConditionsYield
horseradish peroxidase;
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

A

(4-(4-hydroxyphenyl)furoxan-3-yl)methanol
862608-06-8

(4-(4-hydroxyphenyl)furoxan-3-yl)methanol

B

C9H8N2O4

C9H8N2O4

Conditions
ConditionsYield
With sodium nitrite In acetic acid at 25℃; Inert atmosphere;
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

C9H6N2O4

C9H6N2O4

Conditions
ConditionsYield
Stage #1: para-coumaryl alcohol With sodium nitrite In acetic acid at 25℃; Inert atmosphere;
Stage #2: With manganese(IV) oxide In dichloromethane at 25℃; Inert atmosphere;
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

2,2,2-trichloroacetophenone
2902-69-4

2,2,2-trichloroacetophenone

p-hydroxycinnamyl benzoate
189230-69-1

p-hydroxycinnamyl benzoate

Conditions
ConditionsYield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine In acetonitrile at 20 - 25℃; for 12h;0.463g
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

4-(3-(4-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide

4-(3-(4-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
3: trifluoroacetic acid; iso-butanol / 3 h / 100 °C
4: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C
View Scheme
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

3-(4-((2,5-dichloropyrimidin-4-yl)oxy)phenyl)propan-1-ol

3-(4-((2,5-dichloropyrimidin-4-yl)oxy)phenyl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
View Scheme
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

3-(4-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)propan-1-ol

3-(4-((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
3: trifluoroacetic acid; iso-butanol / 3 h / 100 °C
View Scheme
UDP-glucose
133-89-1

UDP-glucose

4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

p‐coumaryl alcohol glucoside

p‐coumaryl alcohol glucoside

Conditions
ConditionsYield
With magnesium chloride; BSA In dimethyl sulfoxide pH=7.5;
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

C9H9ClO

C9H9ClO

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 8 - 20℃;
4-hydroxycinnamic alcohol
3690-05-9

4-hydroxycinnamic alcohol

bis[3-(4-hydroxyphenyl)prop-2-ene]disulphide

bis[3-(4-hydroxyphenyl)prop-2-ene]disulphide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / dichloromethane / 8 - 20 °C
2: sodium hydrogensulfide; triethylamine hydrochloride / methanol / 4 h / 20 °C / Inert atmosphere
View Scheme

3690-05-9Relevant articles and documents

Characterization and Elimination of Undesirable Protein Residues in Plant Cell Wall Materials for Enhancing Lignin Analysis by Solution-State Nuclear Magnetic Resonance Spectroscopy

Kim, Hoon,Padmakshan, Dharshana,Li, Yanding,Rencoret, Jorge,Hatfield, Ronald D.,Ralph, John

, p. 4184 - 4195 (2017)

Protein polymers exist in every plant cell wall preparation, and they interfere with lignin characterization and quantification. Here, we report the structural characterization of the residual protein peaks in 2D NMR spectra in corn cob and kenaf samples and note that aromatic amino acids are ubiquitous and evident in spectra from various other plants and tissues. The aromatic correlations from amino acid residues were identified and assigned as phenylalanine and tyrosine. Phenylalanine's 3/5 correlation peak is superimposed on the peak from typical lignin p-hydroxyphenyl (H-unit) structures, causing an overestimation of the H units. Protein contamination also occurs when using cellulases to prepare enzyme lignins from virtually protein-free wood samples. We used a protease to remove the protein residues from the ball-milled cell walls, and we were able to reveal H-unit structures in lignins more clearly in the 2D NMR spectra, providing a better basis for their estimation.

Action of diverse peroxidases and laccases on six cell wall-related phenolic compounds

Wallace, Graham,Fry, Stephen C.

, p. 769 - 773 (1999)

Four peroxidases and four laccases were compared as to reaction rates catalysed with six phenolic substrates of relevance to the plant cell wall. When each phenolic substrate was tested at 670 μM and pH 6.0, in the presence of 670 μM H2O2 or ~270 μM O2 as the electron acceptor, all the peroxidases and laccases had similar substrate preferences: reaction rates were in the order sinapyl > coniferyl > p-coumaryl alcohols, and feruloyl > p-coumaroyl esters. Specific activities were in the order basic peroxidase > acidic peroxidase>>laccase. The data are consistent with the view that peroxidases rather than laccases play a major role in phenolic cross-linking in the cell wall.

Comparative transcriptomics analysis for gene mining and identification of a cinnamyl alcohol dehydrogenase involved in methyleugenol biosynthesis from asarum sieboldii miq

Liu, Jinjie,Xu, Chong,Zhang, Honglei,Liu, Fawang,Ma, Dongming,Liu, Zhong

, (2018/12/13)

Asarum sieboldii Miq., one of the three original plants of TCM ASARI RADIX ET RHIZOMA, is a perennial herb distributed in central and eastern China, the Korean Peninsula, and Japan. Methyleugenol has been considered as the most important constituent of Asarum volatile oil, meanwhile asarinin is also employed as the quality control standard of ASARI RADIX ET RHIZOMA in Chinese Pharmacopeia. They both have shown wide range of biological activities. However, little was known about genes involved in biosynthesis pathways of either methyleugenol or asarinin in Asarum plants. In the present study, we performed de novo transcriptome analysis of plant tissues (e.g., roots, rhizomes, and leaves) at different developmental stages. The sequence assembly resulted in 311,597 transcripts from these plant materials, among which 925 transcripts participated in ‘secondary metabolism’ with particularly up to 20.22% of them falling into phenylpropanoid biosynthesis pathway. The corresponding enzymes belong to seven families potentially encoding phenylalanine ammonia-lyase (PAL), trans-cinnamate 4-monooxygenase (C4H), p-coumarate 3-hydroxylase (C3H), caffeoyl-CoA O-methyltransferase (CCoAOMT), cinnamoyl-CoA reductase (CCR), cinnamyl alcohol dehydrogenase (CAD), and eugenol synthase (EGS). Moreover, 5 unigenes of DIR (dirigent protein) and 11 unigenes of CYP719A (719A subfamily of cytochrome P450 oxygenases) were speculated to be involved in asarinin pathway. Of the 15 candidate CADs, four unigenes that possessed high FPKM (fragments per transcript kilobase per million fragments mapped) value in roots were cloned and characterized. Only the recombinant AsCAD5 protein efficiently converted p-coumaryl, coniferyl, and sinapyl aldehydes to their corresponding alcohols, which are key intermediates employed not only in biosynthesis of lignin but also in that of methyleugenol and asarinin. qRT-PCR revealed that AsCAD5 had a high expression level in roots at three developmental stages. Our study will provide insight into the potential application of molecular breeding and metabolic engineering for improving the quality of TCM ASARI RADIX ET RHIZOMA.

β-Cyclodextrin/IBX in water: Highly facile biomimetic one pot deprotection of THP/MOM/Ac/Ts ethers and concomitant oxidative cleavage of chalcone epoxides and oxidative dehydrogenation of alcohols

Kumar, Sumit,Ahmed, Naseem

supporting information, p. 648 - 656 (2016/02/12)

A mild and efficient one-pot deprotection of THP/MOM/Ac/Ts ethers, and concomitant oxidative cleavage of epoxides and oxidative dehydrogenation of alcohols to form β-hydroxy 1,2-diketones, 1,2,3-triketones and conjugated aromatic carbonyl systems (chalcones) using β-cyclodextrin/IBX in water has been developed. o-Iodoxybenzoic acid, a readily available hypervalent iodine(v) reagent, was found to be highly effective with β-cyclodextrin in carrying out the deprotection and subsequent transformations under an eco-friendly environment. The reaction gave moderate to excellent yields ranging from 50-99% at 60°C in 40 min to 6 h.

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