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Sigma-Aldrich

15-Hydroxypentadecanoic acid

97%

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About This Item

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

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
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)
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)
Zeolite-catalyzed macrolactonization of Ookoshi T and Onaka M. ω-hydroxyalkanoic acids in a highly concentrated solution.
Ookoshi T and Onaka M.
Tetrahedron Letters, 39(3), 293-296 (1998)
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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