14436-32-9 Usage
Description
9-Decenoic acid, also known as decenoic acid, is a monocarboxylic fatty acid with a double bond located at the 9th carbon atom. It is characterized by its waxy, somewhat fruity, and milky odor. 9-Decenoic acid is found in various food products, including butterfat, Swiss, blue, cheddar, Romano, and Parmesan cheeses, as well as goat, sheep, and other cheeses, mutton, hop oil, beer, and both white and red wine. It is known for its unique taste characteristics, which include a waxy, creamy, fatty flavor with a cheesy and milky nuance at a taste threshold value of 40 ppm.
Uses
1. Pharmaceutical Industry:
9-Decenoic acid is used as a key intermediate in the synthesis of epothilones A and B, which are potent anticancer agents. These compounds are prepared through a series of chemical reactions, including macroaldolization, olefin metathesis, and macrolactonization. Epothilones have shown promise in the treatment of various types of cancer due to their ability to stabilize microtubules and inhibit cell division.
2. Analgesic Applications:
9-Decenoic acid is also used in the synthesis of potent, selective, and efficacious reversible α-ketoheterocycle inhibitors of fatty acid amide hydrolase (FAAH). These inhibitors have been found to be effective as analgesics, providing pain relief through their interaction with the endocannabinoid system.
3. Flavor Industry:
Due to its unique taste characteristics, 9-Decenoic acid can be used as a flavoring agent in the food and beverage industry. Its waxy, creamy, fatty flavor with a cheesy and milky nuance can be utilized to enhance the taste of various products, such as cheeses, dairy products, and even alcoholic beverages like beer and wine.
4. Cosmetics and Personal Care Industry:
Given its waxy and creamy properties, 9-Decenoic acid can be used as an ingredient in the formulation of cosmetics and personal care products, such as creams, lotions, and balms. Its emollient and moisturizing properties can help improve the texture and feel of these products, providing a smooth and luxurious experience for the user.
Synthesis Reference(s)
Synthetic Communications, 9, p. 63, 1979 DOI: 10.1080/00397917908064130Tetrahedron Letters, 25, p. 3207, 1984 DOI: 10.1016/S0040-4039(01)91010-X
Check Digit Verification of cas no
The CAS Registry Mumber 14436-32-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,4,3 and 6 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 14436-32:
(7*1)+(6*4)+(5*4)+(4*3)+(3*6)+(2*3)+(1*2)=89
89 % 10 = 9
So 14436-32-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2H,1,3-9H2,(H,11,12)
14436-32-9Relevant articles and documents
Synthesis of highly fluorinated fatty acid esters of glycerol:glycerol tripalmitate-F39
Rastegar, Majid F.,Buchanan, Gerald W.,Bouffard, Melanie C.
, p. 1042 - 1045 (2006)
Glycerol tripalmitate-F39 has been prepared from glycerol and the acid chloride of RF-palmitic acid-F13 via a solid phase aluminum oxide catalyzed reaction. The product has been characterized by electrospray mass spectrometry and 1H, 19F and 13C NMR methods. A second, less efficient synthesis is reported in which a chain elongation strategy is employed after reaction of glycerol with the acid chloride of 9-decenoic acid.
EXTRAHEPATIC DELIVERY
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Paragraph 0566; 0656, (2021/05/15)
One aspect of the present invention relates to a compound comprising an antisense strand which is complementary to a target gene; a sense strand which is complementary to said antisense strand; and one or more lipophilic monomers, containing one or more lipophilic moieties, conjugated to one or more positions on at least one strand, optionally via a linker or carrier. Another aspect of the invention relates to a method of gene silencing, comprising administering to a cell or a subject in need thereof a therapeutically effective amount of the lipophilic monomer-conjugated compound.
One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols
Inada, Haruki,Furukawa, Keisuke,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 15105 - 15108 (2019/12/26)
Herein, we report the nor-AZADO-catalyzed exhaustive aerobic oxidations of 1,2-diols to α-keto acids. Combining oxidation with transamination using dl-2-phenylglycine led to the synthesis of free α-amino acids (AAs) in one pot. This method enables the rapid and flexible preparation of a variety of valuable unnatural AAs, such as fluorescent AAs, photoactivatable AAs, and other functional AAs for bioorthogonal reactions.
METHOD OF SYNTHESISING AMINO ACID BY METATHESIS, HYDROLYSIS, THEN HYDROGENATION
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Paragraph 0182-0186, (2016/03/05)
A method of synthesising an amino acid from an unsaturated fatty compound I that includes at least the following steps: cross-metathesis with a short unsaturated compound II, one of compounds I or II comprising a nitrile function and the other of these compounds II or I an ester function, so as to obtain and recover at least one monounsaturated nitrile ester NEU; hydrolysis of the NEU in unsaturated acid nitrile NAU; hydrogenation of the NAU to saturated amino acid AA; and then purification of the AA, if applicable, in particular by crystallisation. Also, a polymer obtained by polymerisation using the amino acid synthesised according to the method.
