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 
• 13019-22-2 9-Decen-1-ol 
• 25601-41-6 methyl 9-decenoate 
• 112-80-1 cis-Octadecenoic acid 
• 74-85-1 ethene 
• 89359-54-6 9-bromo-1-nonene 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 17643-36-6 9-decyn-1-ol 
• 1852-04-6 undecanedioic acid 
• 373-49-9 cis-9-hexadecenoic acid 
• 112-38-9 10-undecenoic acid 
• 26825-94-5 10-bromodecanoic acid methyl ester 
• 50530-12-6 10-bromodecanoic acid 

Downstream Products

• 1642-49-5 dec-9-ynoic acid 
• 206867-03-0 N-(8-nonenylcarbonyl)-N'-benzyl-N-(4-methoxybenzyl)iminodiacetic acid diamide 
• 65371-24-6 phoracantholide I 
• 134781-57-0 S-Phenyl 9-Hydroxydecanethioate 
• 134781-61-6 Pentachlorophenyl 9-Azidodecanoate 
• 2575-07-7 methyl 9-oxodecanoate 
• 1067658-92-7 N-methyl-((S)-piperid-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 4494-16-0 1,18-octadec-9-enedioic acid 
• 1120-12-3 9-aminononanoic acid 
• 25601-41-6 methyl 9-decenoate 
• 4900-30-5 nona-1,8-diene 
• 1584730-65-3 C₃₄H₄₂O₄Si 
• 1584730-63-1 C₃₄H₄₂O₄Si 
• 1584730-61-9 C₃₄H₄₂O₄Si 

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

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.

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.

One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols

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.

RENEWABLY DERIVED POLYAMIDES AND METHODS OF MAKING THE SAME

Methods of making polyamides from renewable materials, such as natural oils, are generally disclosed herein. In some embodiments, the polyamides are nylon-10. In some such embodiments, nylon-10 is made by polymerizing 10-aminodecanoic acid, or esters thereof. In some further such embodiments, the 10-aminodecanoic acid monomers (or esters thereof) are derived from natural oils via the metathesis of unsaturated fatty acid moieties of the natural oil.

METHOD OF SYNTHESISING AMINO ACID BY METATHESIS, HYDROLYSIS, THEN HYDROGENATION

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.

Ring-closing metathesis based total synthesis of ciliatamides A and B and their structural confirmation

Protecting group dependant ring-closing metathesis based approach to the total synthesis of the revised structures of ciliatamides A and B has been described. The current synthetic strategy utilizes the amino acid as starting material to introduce both the stereogenic centers. However, usage of non-racemizing reagents (EDC·HCl, HATU/NMM); for amide coupling and Grubbs' second generation catalyst for caprolactam ring synthesis makes the present approach more convenient to get the correct conclusion on absolute stereochemistry. Thus, on the basis of similar optical rotation values with the Lindsley's reported data, this synthesis further supported for the actual stereochemistry of both ciliatamides A and B is (R,R).

Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes

The biocatalytic oxidative tandem decarboxylation of C7–C18dicarboxylic acids to terminal C5–C16dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene; scale-up allowed the isolation of 1,15-hexadecadiene and 1,11-dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.

METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS

The invention relates to a method for preparing a compound of formula (I), wherein n is an integer from 1 to 21,said method comprises reacting a light olefin fraction, in the presence of a metathesis catalyst, with a compound having from 10 to 24 carbon atoms, of the following formula (II): wherein, n is an integer from 1 to 21,R corresponds to a hydrogen atom or an alkyl or alkenyl chain from 1 to20 carbon atoms optionally substituted by at least one hydroxyl group, said compound of formula (II) being used alone or in a mixture of compounds of formula (II).