14436-32-9

Basic information

• Product Name: 9-DECENOIC ACID
• Synonyms: Decenoicacid;9-DECENOIC ACID 88+%;9-DECENOIC ACID 90%;9-Decylenic acid;Caproleic acid;FEMA 3660;FEMA NUMBER 3660;9-DECENOIC ACID
• CAS NO: 14436-32-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 238-410-9
• Product Categories: omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Unsaturated Carboxylic Acids;Alphabetical Listings;C-D;Flavors and Fragrances
• Mol File: 14436-32-9.mol

Chemical Properties

• Melting Point: 26.5°C
• Boiling Point: 270 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.918 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0185mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: 9-DECENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9-DECENOIC ACID(14436-32-9)
• EPA Substance Registry System: 9-DECENOIC ACID(14436-32-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 14436-32-9(Hazardous Substances Data)

Usage

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

InChI:InChI=1/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2H,1,3-9H2,(H,11,12)

Upstream product

• 1679-53-4 10-hydroxydecanoic acid 
• 69695-27-8 2-hydroxy-10-undecenoic acid 
• 76786-04-4 1,1-Diphenyl-decan-1,9-dien 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 13019-22-2 9-Decen-1-ol 
• 112-80-1 cis-Octadecenoic acid 
• 74-85-1 ethene 
• 1852-04-6 undecanedioic acid 
• 89359-54-6 9-bromo-1-nonene 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 17643-36-6 9-decyn-1-ol 
• 373-49-9 cis-9-hexadecenoic acid 
• 112-38-9 10-undecenoic acid 
• 26825-94-5 10-bromodecanoic acid methyl ester 

Downstream Products

• 25601-41-6 methyl 9-decenoate 
• 334-48-5 1-decanoic acid 
• 1422-27-1 9-hydroxydecanoic acid 
• 206867-03-0 N-(8-nonenylcarbonyl)-N'-benzyl-N-(4-methoxybenzyl)iminodiacetic acid diamide 
• 123-99-9 azelaic acid 
• 64-18-6 formic acid 
• 65371-24-6 phoracantholide I 
• 134781-57-0 S-Phenyl 9-Hydroxydecanethioate 
• 134781-61-6 Pentachlorophenyl 9-Azidodecanoate 
• 2575-07-7 methyl 9-oxodecanoate 
• 95227-27-3 1,1-Diphenyl-decan-1,9-dien 
• 1067658-92-7 N-methyl-((S)-piperid-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 1067658-94-9 N-methyl-((R)-piperid-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 1008161-89-4 N-methyl-((R)-piperid-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)dec-9-enamide 

Relevant articles and documents

Synthesis of highly fluorinated fatty acid esters of glycerol:glycerol tripalmitate-F39

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.

Synthesis of site-specifically13C labeled linoleic acids

Soybean lipoxygenase-1 (SLO-1) catalyzes the C–H abstraction from the reactive carbon (C-11) in linoleic acid as the first and rate-determining step in the formation of alkylhydroperoxides. While previous labeling strategies have focused on deuterium labeling to ascertain the primary and secondary kinetic isotope effects for this reaction, there is an emerging interest and need for selectively enriched13C isotopologues. In this Letter, we present synthetic strategies for site-specific13C labeled linoleic acid substrates. We take advantage of a Corey–Fuchs formyl to terminal13C-labeled alkyne conversion, using13CBr4as the labeling source, to reduce the number of steps from a previous fatty acid13C synthetic labeling approach. The labeled linoleic acid substrates are useful as nuclear tunneling markers and for extracting active site geometries of the enzyme–substrate complex in lipoxygenase.

EXTRAHEPATIC DELIVERY

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RENEWABLY DERIVED POLYAMIDES AND METHODS OF MAKING THE SAME

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METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS

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