499-44-5 Usage
Description
Hinokitiol, also known as β-thujaplicin, is a natural monoterpenoid derived from the wood of trees in the Cupressaceae family. It is a tropolone derivative and one of the thujaplicins, characterized by its antimicrobial properties and unique chemical structure.
Uses
Used in Antimicrobial Applications:
Hinokitiol is used as an antimicrobial agent for its inhibitory effects on various microorganisms, including Chlamydia trachomatis. This makes it potentially useful as a topical drug in the medical field.
Used in Food Industry:
Hinokitiol is used as an antibacterial additive in the food industry to maintain freshness and prevent spoilage, ensuring the safety and quality of the products.
Used in Cosmetics:
In the cosmetics industry, Hinokitiol is utilized for its antimicrobial and preservative properties, helping to extend the shelf life and maintain the integrity of cosmetic products.
Used in Oral Care:
Hinokitiol is used in oral care products, such as toothpaste, due to its antibacterial properties, which help maintain oral hygiene and prevent dental issues.
Used in Skin Care:
Hinokitiol is used in skin care products for its antimicrobial and preservative properties, promoting skin health and preventing the growth of harmful microorganisms on the skin.
Used in Eye Care:
Hinokitiol is used in eye drops for its antimicrobial properties, helping to maintain eye health and prevent infections.
Used in Japan as a Food Additive:
Hinokitiol is also used as a food additive in Japan, where it is recognized for its antimicrobial and preservative qualities, contributing to the safety and longevity of the products.
benefits
Hinokitiol (β-thujaplicin) is a naturally occurring antioxidant, found in the heartwood of certain plants. It acts as a metal chelator and, also, enhances the activity of superoxide dismutase (Huang et al., 2015). It was found to be very protective in the assay. It has not been previously studied as a HC protectant. In addition to its antioxidant properties, hinokitiol has been shown to reduce inflammation via suppression of NFκB, and metalloproteinases, and to activate caspase 3. The former activities could contribute to its protective effect.Hinokitiol is a superpower ingredient that has anti-inflammatory, antioxidant, antibacterial, anti-fungal and anti-melanogenic properties. Best of all, hinokitiol is as gentle as it is powerful. Hinokitiol’s properties allow it to target the inflammatory redness and blemishes seen in rosacea and acne. Hinokitiol is effective against P. acnes bacteria, and there is no known acquired resistance to it, unlike other prescription antibiotics.
Safety
The safety of hinokitiol has been tested in rats and no carcinogenic effect to rats was found.In 2006, hinokitiol was categorized under the Domestic substances list (DSL) in Canada as non-persistent, non-bioaccumulative and non-toxic to aquatic organisms.
Anticancer Research
Studied in xenograft tumors such lung adenocarcinoma cell, EGFR-TKI-resistantlines PC9-IR and H1975 in which the growth inhibition was observed, a novel antitumormechanism was hypothesized. In summary, the hinokitiol can induce DNAdamage and autophagy (Rodrigues et al. 2015).
References
1) Ido et al (1999) Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3; Cell Prolif., 32 63
2) Suzuki et al. (2000) Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase; Biochem. Biophys. Res. Commun., 275 885
3) Morita et al. (2007) The mechanism of the bactericidal activity of hinokitiol; Biocontrol Sci., 12 101
4) Liu and Yamauchi (2006) Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines; Biochem. Biophys. Res. Commun., 351 26
5) Lee et al. (2010) Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases; Biochem. Biophys. Res. Commun., 396 370
Check Digit Verification of cas no
The CAS Registry Mumber 499-44-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 9 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 499-44:
(5*4)+(4*9)+(3*9)+(2*4)+(1*4)=95
95 % 10 = 5
So 499-44-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
499-44-5Relevant articles and documents
Franck-Neumann et al.
, p. 5033 (1978)
Preparation method of beta-thujaplicine
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Paragraph 0028; 0029; 0030; 0031; 0032; 0035; 0036, (2018/11/03)
The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of beta-thujaplicine. The preparation method comprises the steps that tri-n-propylamine, glacial acetic acid and water serve as reaction reagents, and a ring enlargement reaction occurs by 7,7-dichloro-3-isopropylbicycle[3.2.0]heptyl-2-ene-6-one (the compound structure is shown in formula 2).
A high-purity chinese juniper methyl alcohol of preparation method (by machine translation)
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, (2018/08/03)
The invention discloses a method for preparing high-purity chinese juniper methyl alcohol, cyclopentadiene activated reagent after activation with isopropyl bromine instead should be containing various isomers of the isopropyl cyclopentadiene, then in the isomer conversion catalyst under the action of the isomerization reaction to obtain 1 - isopropyl cyclopentadiene; 1 - isopropyl cyclopentadiene and [...] react 1 - isopropyl cyclopentadiene and 4, 4 - [...] 5 - one; 1 - isopropyl cyclopentadiene and 4, 4 - [...] 5 - ketone with triethylamine heating reflux generating ring enlargement reaction to obtain the target product chinese juniper methyl alcohol. The invention raw materials used are cheap and easily obtained, and the step A through the isomer of a hydrocarbon conversion catalyst in use significantly reduces the by-product 2 - isopropyl cyclopentadiene and 5 - isopropyl cyclopentadiene generation, improves the yield of products, and Ru (Ac)3 - ZSM - 5 can be repeatedly used for four times still maintains good catalytic activity; step B by adjusting reaction solution in glacial acetic acid, effectively prevent the emergence of the diketone by-product. (by machine translation)