392979

15-Hydroxypentadecanoic acid

97%

• Linear Formula: HO(CH₂)₁₄CO₂H
• CAS Number: 4617-33-8
• Molecular Weight: 258.40
• EC Number: 225-026-1
• MDL number: MFCD00039535
• UNSPSC Code: 12352100
• PubChem Substance ID: 24864154
• NACRES: NA.22

Properties

• assay: 97%
• mp: 85-89 °C (lit.)
• functional group: carboxylic acid; hydroxyl
• SMILES string: OCCCCCCCCCCCCCCC(O)=O
• InChI: 1S/C15H30O3/c16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15(17)18/h16H,1-14H2,(H,17,18)
• InChI key: BZUNJUAMQZRJIP-UHFFFAOYSA-N

Description

General description

15-Hydroxypentadecanoic acid is an ω-hydroxy acid. One of the method reported for its synthesis is from 1,12-dodecanolide. It is reported to be one of the bioactive component in Tagetes erecta L. leaf and flower extract.

15-Hydroxypentadecanoic acid undergoes lactonization reaction catalyzed by Mucor javanicus L46 and Mucor miehei to afford macrocyclic mono- and oligolactone derivatives. Its lipase-catalyzed synthesis from 15-tetracosenoic acid in Malania Olcifera Chum oil has been proposed. It also participates in the biosynthesis of pentadecanolide.

Application

15-Hydroxypentadecanoic acid is suitable reagent used in the following studies:

• As an internal standard in the quantification of formation of 11-hydroxylauric acid by gas chromatography.
• In the synthesis of [16-¹⁴C]16DCA (DCA= dicarboxylic acid) by one-carbon elongation procedure at C15.
• As an internal standard for the normalization of intensities in the mass spectra of plant cutin polymer.

It may be used in the synthesis of 5-pentadecanolide on dealuminated HY zeolite and also fatty acid analog of podophyllotoxin.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)