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392979

Sigma-Aldrich

15-Hydroxypentadecanoic acid

97%

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About This Item

Linear Formula:
HO(CH2)14CO2H
CAS Number:
Molecular Weight:
258.40
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

mp

85-89 °C (lit.)

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sacha Ferdinandusse et al.
Journal of lipid research, 45(6), 1104-1111 (2004-04-03)
Dicarboxylic acids (DCAs) are omega-oxidation products of monocarboxylic acids. After activation by a dicarboxylyl-CoA synthetase, the dicarboxylyl-CoA esters are shortened via beta-oxidation. Although it has been studied extensively where this beta-oxidation process takes place, the intracellular site of DCA oxidation
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
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)
Dušan Veličković et al.
The Plant journal : for cell and molecular biology, 80(5), 926-935 (2014-10-04)
The cutin polymers of different fruit cuticles (tomato, apple, nectarine) were examined using matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI MSI) after in situ release of the lipid monomers by alkaline hydrolysis. The mass spectra were acquired from each coordinate
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)

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