5455-97-0

Basic information

• Product Name: 12-ketooleic acid
• Synonyms: 12-ketooleic acid;(Z)-12-Oxo-9-octadecenoic acid
• CAS NO: 5455-97-0
• Molecular Formula: C₁₈H₃₂O₃
• Molecular Weight: 296.44
• Mol File: 5455-97-0.mol

Chemical Properties

• Boiling Point: 409.9°Cat760mmHg
• Flash Point: 215.9°C
• Appearance: /
• Density: 0.953g/cm³
• Vapor Pressure: 7.23E-08mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: 12-ketooleic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 12-ketooleic acid(5455-97-0)
• EPA Substance Registry System: 12-ketooleic acid(5455-97-0)

Safety Data

• Hazardous Substances Data: 5455-97-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
12-ketooleic acid is used as a potential therapeutic agent for its anti-inflammatory and antioxidant properties, which may contribute to the treatment of various inflammatory and oxidative stress-related conditions.
Used in Cosmetic Formulations:
In the cosmetic industry, 12-ketooleic acid is utilized as an active ingredient for its role in skin health. Its presence in human skin and its association with aging and wrinkle formation make it a valuable component in anti-aging and skin care products aimed at reducing the appearance of wrinkles and promoting a more youthful complexion.
Used in Skin Care Research:
12-ketooleic acid is employed as a subject of study in skin care research to better understand its impact on skin aging processes. This knowledge can lead to the development of more effective treatments and preventative measures against skin aging and the formation of wrinkles.
Used in Lipid Metabolism Studies:
Given its identification in plants and potential role in lipid metabolism, 12-ketooleic acid is used as a subject in biological research to explore its function and potential applications in managing lipid profiles and related metabolic processes.

InChI:InChI=1/C18H32O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-

Upstream product

• 141-22-0 Ricinoleic acid 
• 68396-17-8 12-oxo-octadec-9-ynoic acid 
• 112-38-9 10-undecenoic acid 
• 2528-61-2 Heptanoic acid chloride 
• 925-42-8 12-hydroxyoctadec-9-ynoic acid 
• 540-13-6 (R)-12-hydroxy-octadec-9-ynoic acid 
• 141-24-2 methyl ricinoleate 

Downstream Products

• 21308-79-2 methyl 12-oxo-octadec-trans-10-enoate 
• 6114-39-2 methyl 12-hydroxyoctadecanoate 
• 112-61-8 Methyl stearate 
• 123-99-9 azelaic acid 
• 4179-48-0 9,12-Dioxo-octadecanoic acid 
• 5416-59-1 threo-10,11-dihydroxy-9,12-dioxo-octadecanoic acid 
• 5416-58-0 (+/-)-threo-10,11-epoxy-12-oxo-octadecanoic acid 
• 81212-19-3 (Z)-12-hydroxyoctadec-9-enoic acid 
• 28833-56-9 9,12-dioxooctadec-trans-10-enoic acid 
• 65187-02-2 12-oxo-octadec-trans-10-enoic acid 

Relevant articles and documents

Enzyme Cascade Reactions for the Biosynthesis of Long Chain Aliphatic Amines from Renewable Fatty Acids

Enzyme cascade reactions for the synthesis of long chain aliphatic amines such as (Z)-12-aminooctadec-9-enoic acid, 10- or 12-aminooctadecanoic acid, and 10-amino-12-hydroxyoctadecanoic acid from renewable fatty acids were investigated. (Z)-12-aminooctadec-9-enoic acid was produced from ricinoleic acid ((Z)-12-hydroxyoctadec-9-enoic acid) via (Z)-12-ketooctadec-9-enoic acid with a conversion of 71% by a two-step in vivo biotransformation involving a long chain secondary alcohol dehydrogenase (SADH) from Micrococcus luteus and a variant of the amine transaminase (ATA) from Vibrio fluvialis. 10-Aminooctadecanoic acid was prepared from oleic acid ((Z)-octadec-9-enoic acid) via 10-hydroxyoctadecanoic acid and 10-ketooctadecanoic acid by an in vivo three-step biocatalysis reaction involving not only the SADH and ATA variants, but also a fatty acid double bond hydratase (OhyA) from Stenotrophomonas maltophilia. 10-Aminooctadecanoic acid was produced at a total rate of 4.4 U/g dry cells with a conversion of 87% by recombinant Escherichia coli expressing the SADH and ATA variants, and OhyA simultaneously. In addition, bulky aliphatic amines could also be produced by the isolated enzymes (i. e., the SADH, the ATA variants, and a nicotinamide adenine dinucleotide (NADH) oxidase from Lactobacillus brevis) with methylbenzylamine or benzylamine as amino donor. This study thus contributes to the biosynthesis of long chain aliphatic amines having two large substituents next to the amine functionality. (Figure presented.).

Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (R)-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid

Regiospecific oxyfunctionalization of renewable long chain fatty acids into industrially relevant C9 carboxylic acids has been investigated. One example was biocatalytic transformation of 10,12-dihydroxyoctadecanoic acid, which was produced from ricinoleic acid ((9Z,12R)-12-hydroxyoctadec-9-enoic acid) by a fatty acid double bond hydratase, into (R)-3-hydroxynonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid with a high conversion yield of ca. 70%. The biotransformation was driven by enzyme/whole-cell biocatalysts, consisting of the esterase of Pseudomonas fluorescens and the recombinant Escherichia coli expressing the secondary alcohol dehydrogenase of Micrococcus luteus, the Baeyer-Villiger monooxygenase of Pseudomonas putida KT2440 and the primary alcohol/aldehyde dehydrogenases of Acinetobacter sp. NCIMB9871. The high conversion yields and the high product formation rates over 20 U/g dry cells with insoluble reactants indicated that various (poly-hydroxy) fatty acids could be converted into multi-functional products via the simultaneous enzyme/whole-cell biotransformations. This study will contribute to the enzyme-based functionalization of hydrophobic substances. (Figure presented.).

Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD+-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with α- or β-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 μM with a kcat of 7.6 × 10-3 s-1. The apparent Km value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 μM with a kcat of 5.7 × 10-1 s-1. In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group.

Alkylaluminium Dichloride Induced Friedel-Crafts Acylation of Unsaturated Carboxylic Acids and Alcohols

The ethylaluminium dichloride induced Friedel-Crafts acylation of unsaturated carboxylic acids, for example 10-undecenoic acid (1a) and oleic acid (5a), and of the respective alcohols 1b and 5b with acyl chlorides and cyclic acyl anhydrides gave the corresponding long-chain β,γ-unsaturated ketones 3, 6/7, 11 and 13/14 with ω-carboxy and ω-hydroxy functions, respectively.The intramolecular cyclization of petroselinic acid chloride (17) yielded (E)-2-dodecylidenecyclohexanone (18).Catalytic hydrogenation gave the respective saturated ketones 4, 8/9, 12, 15/16 and 19.Key Words: Friedel-Crafts acylation / β,γ-Unsaturated keto carboxylic acids and alcohols

Derivatization of Keto Fatty Acids: Part XI - Reaction of Ethanedithiol with α-Bromo, α,β-Unsaturated and β,γ-Unsaturated Ketones

Sulphur derivatives containing both the dithiolane and thioether moieties have been prepared by the reaction of ethanedithiol with α-bromoketone and α,β- and β,γ-unsaturated ketones.Reaction of ethanedithiol with 11-bromo-10-oxoundecanoic acid (I) gives the corresponding dithiolane containing thioether moiety at α-position as a major product (IV) alongwith a bromine containing noncyclised compound as a minor product (V).Methyl 4-oxo-trans-2-octadecenoate (II) reacts with the reagent and yields methyl 4-dithiolane-2(3)-thiolethylthiooctadecanoate (VI) alongwith methyl 4-dithiolane-trans-2-octadecenoate (VII) as minor product. 12-Oxo-cis-9-octadecenoic acid (III) is also found to react readily with ethanedithiol and affords 12-dithiolane-9(10)-thioacetoxyethylthiooctadecanoic acid (IX) and 12-dithiolane-9(10)-thiolethylthiooctadecanoic acid (X) as major and minor products, respectively.The spectral (IR, NMR, mass) data of the individual reaction products have been discussed.

Stereochemistry of Olefin and Fatty Acid Oxidation. Part 3. The Allylic Hydroperoxides from the Autoxidation of Methyl Oleate

Methods have been developed, using 13C n.m.r. spectroscopy and mass spectrometry, for the analysis of all eight cis and trans allylic 8-, 9-, 10-, and 11-hydroperoxides formed on autoxidation of methyl oleate.