392979
15-Hydroxypentadecanoic acid
97%
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About This Item
Linear Formula:
HO(CH2)14CO2H
CAS Number:
Molecular Weight:
258.40
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
225-026-1
MDL number:
InChI key
BZUNJUAMQZRJIP-UHFFFAOYSA-N
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)
SMILES string
OCCCCCCCCCCCCCCC(O)=O
assay
97%
mp
85-89 °C (lit.)
functional group
carboxylic acid, hydroxyl
Quality Level
Related Categories
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Preparation of 15-hydroxypentadecanoic acid by means of condensation reaction via β-ketosulfoxide.
Nozaki H, et al.
Canadian Journal of Chemistry, 46(23), 3767-3770 (1968)
Screening and evaluation of bioactive components of Tagetes erecta L. by GC-MS analysis.
Devika R and Kovilpillai J.
Asian Journal of Pharmaceutical and Clinical Research, 7(2), 58-60 (2014)
Enzymatic lactonization of 15-hydroxypentadecanoic and 16-hydroxyhexadecanoic acids to macrocyclic lactones.
Antczak U, et al.
Enzyme and Microbial Technology, 13(7), 589-593 (1991)
Lipase catalyzed synthesis of pentadecanolide from 15-hydroxypentadecanoic acid.
Pan XB, et al.
Chinese Journal of Applied Chemistry / Ying Yong Hua Xue, 21(8), 850-852 (2004)
Jamal Mustafa et al.
Lipids, 39(2), 167-172 (2004-05-12)
Derivatives of podophyllotoxin were prepared by coupling 10 FA with the C4-alpha-hydroxy function of podophyllotoxin. The coupling reactions between FA and podophyllotoxin were carried out by dicyclohexylcarbodiimide in the presence of a catalytic amount of dimethylaminopyridine to produce quantitative yields
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