10075-07-7

Basic information

• Product Name: (9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester
• Synonyms: (9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester;[10E,12Z,S,(+)]-9-Hydroxy-10,12-octadecadienoic acid methyl ester
• CAS NO: 10075-07-7
• Molecular Formula: C₁₉H₃₄O₃
• Molecular Weight: 310.47
• Mol File: 10075-07-7.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester(10075-07-7)
• EPA Substance Registry System: (9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester(10075-07-7)

Safety Data

• Hazardous Substances Data: 10075-07-7(Hazardous Substances Data)

Usage

Description

(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester is a methyl ester derivative of a hydroxy fatty acid, characterized by an unsaturated carbon chain with a hydroxy group and two double bonds. (9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester is commonly found in natural products such as plant oils and can be synthesized in the laboratory.

Uses

Used in Pharmaceutical Industry:
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester is used as a precursor for the synthesis of bioactive compounds due to its potential biological activity and ability to influence cellular processes.
Used in Cosmetic Industry:
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester serves as a starting material for the production of surfactants and emulsifiers, which are essential in formulating various cosmetic products to ensure stability, texture, and effectiveness.
Used in Industrial Applications:
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acid methyl ester is utilized in the synthesis of other compounds for various industrial uses, highlighting its versatility and importance in chemical manufacturing.

Upstream product

• 186581-53-3 diazomethane 
• 60-33-3 linoleic acid 
• 63318-29-6 (Z)-1-iodohept-1-ene 
• 136031-77-1 (E)-9-Hydroxy-11-iodo-undec-10-enoic acid methyl ester 
• 25152-83-4 (2E,4Z)-2,4-decadienal 
• 59321-71-0 1,7-Heptandiylbis(magnesiumbromid) 
• 112-63-0 Methyl linoleate 
• 53613-56-2 9-hydroxyundec-10-enoic acid methyl ester 
• 109921-65-5 (Z)-hept-1-enylmagnesium bromide 
• 84999-72-4 methyl (9E)-11-hydroxyundec-9-enoate 
• 119125-33-6 methyl (9E,12Z)-11-acetoxyoctadeca-9,12-dienoate 
• 123-99-9 azelaic acid 
• 56555-02-3 methyl 9-chloro-9-oxononanoate 
• 2104-19-0 azelaic monomethyl ester 

Downstream Products

• 6084-82-8 (R)-9-hydroxy-(10E,12Z)-10,12-octadecadienoic acid methyl ester 
• 98442-95-6 benzoate of 9-hydroxy-(E)-10-(Z)-12-octadecadienoic acid methy ester 
• 403619-52-3 Benzoic acid (2E,4Z)-(R)-1-(7-methoxycarbonyl-heptyl)-deca-2,4-dienyl ester 
• 99530-30-0 methyl 9-benzoyloxylinoleate 
• 15514-85-9 (9R,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid 
• 5204-87-5 Octadeca-8t,10t,12c-triensaeure 

Relevant articles and documents

Isolation of 9-hydroxy-10E,12Z-octadecadienoic acid, an inhibitor of fat accumulation from Valeriana fauriei

An EtOH extract of Valeriana fauriei was found to exhibit potent inhibition of fat accumulation against 3T3-L1 murine adipocytes. After performing several chromatographic steps, we successfully isolated the conjugated linoleic acid derivative, 9-hydroxy-10E,12Z-octadecadienoic acid (9-HODE). Synthesized 9-HODE and its analogs showed inhibitory activity against fat accumulation.

Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia

Bioassay-guided separation from the MeOH extract of the South American medicinal plant Sida cordifolia resulted in isolation of (10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (1) as an unprecedented NES non-antagonistic inhibitor for nuclear export of Rev. This mechanism of action was established by competitive experiment by the biotinylated probe derived from leptomycin B, the known NES antagonistic inhibitor. Additionally, structure-activity relationship analysis by use of the synthesized analogs clarified cooperation of several functionalities in the Rev-export inhibitory activity of 1.

Synthesis and biological activity of hydroxylated derivatives of linoleic acid and conjugated linoleic acids

Allylic hydroxylated derivatives of the C18 unsaturated fatty acids were prepared from linoleic acid (LA) and conjugated linoleic acids (CLAs). The reaction of LA methyl ester with selenium dioxide (SeO2) gave mono-hydroxylated derivatives, 13-hydroxy-9Z,11E-octadecadienoic acid, 13-hydroxy-9E,11E-octadecadienoic acid, 9-hydroxy-10E,12Z-octadecadienoic acid and 9-hydroxy-10E,12E-octadecadienoic acid methyl esters. In contrast, the reaction of CLA methyl ester with SeO2 gave di-hydroxylated derivatives as novel products including, erythro-12,13-dihydroxy-10E-octadecenoic acid, erythro-11,12-dihydroxy-9E-octadecenoic acid, erythro-10,11-dihydroxy-12E-octadecenoic acid and erythro-9,10-dihydroxy-11E-octadecenoic acid methyl esters. These products were purified by normal-phase short column vacuum chromatography followed by high-performance liquid chromatography (HPLC). Their chemical structures were characterized by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR). The allylic hydroxylated derivatives of LA and CLA exhibited moderate in vitro cytotoxicity against a panel of human cancer cell lines including chronic myelogenous leukemia K562, myeloma RPMI8226, hepatocellular carcinoma HepG2 and breast adenocarcinoma MCF-7 cells (IC50 10-75 μM). The allylic hydroxylated derivatives of LA and CLA also showed toxicity to brine shrimp with LD50 values in the range of 2.30-13.8 μM. However these compounds showed insignificant toxicity to honeybee at doses up to 100 μg/bee.

Synthesis of keto- and hydroxydienoic compounds from linoleic acid

A convenient preparative method has been developed for the synthesis of hydroxydienoic (9-HODE and 13-HODE) and ketodienoic compounds (9-KODE and 13-KODE) from natural linoleic acid. Methyl linoleate was treated with 1.25 eq. of m-chloroperbenzoic acid in alcoholic solution, giving a mixture of mono-epoxides (yield 60%), that was treated with a solution of HBr in MeOH to yield a mixture of the bromohydrins (yield 92%). The last was oxidized by Jones reagent to a mixture of bromoketones (yield 64%) and the mixture obtained was dehydrobrominated by DBU to produce a mixture of ketodienoic compounds (yield 94%). Reduction of the ketodienoic compounds by KBH4 in MeOH led to the corresponding hydroxydienoic (9-HODE and 13-HODE) methyl esters (yield 83%). The synthetic approach described is simple and gives reliable results. The keto- and hydroxy fatty acids obtained were characterized thoroughly by TLC, HPLC, UV, FT-IR, 1H-, 1H1H- and 13C-NMR.