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807788

Sigma-Aldrich

palmitic-acid-9-hydroxy-stearic-acid

95%

Synonym(s):

9-PAHSA

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About This Item

Empirical Formula (Hill Notation):
C34H66O4
Molecular Weight:
538.89
UNSPSC Code:
12352106
PubChem Substance ID:
329768748
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

mp

33.5 °C

storage temp.

2-8°C

SMILES string

CCCCCCCCCC(OC(CCCCCCCCCCCCCCC)=O)CCCCCCCC(O)=O

InChI

1S/C34H66O4/c1-3-5-7-9-11-12-13-14-15-16-18-23-27-31-34(37)38-32(28-24-20-17-10-8-6-4-2)29-25-21-19-22-26-30-33(35)36/h32H,3-31H2,1-2H3,(H,35,36)

InChI key

MHQWHZLXDBVXML-UHFFFAOYSA-N

General description

Palmitic-acid-9-hydroxy-stearic-acid (9-PAHSA) is an isomeric form of bioactive fatty acid ester of hydroxyl-fatty acid (FAHFA).

Application

9-PAHSA is composed of palmitic acid attached to stearic acid and is in the class of branched lipids referred to as fatty acid esters of hydroxy fatty acids (FAHFAs). 9-PAHSA was found at increased levels in serum and white adipose tissue of insulin-sensitive mice. Levels were found to be lower in white adipose tissue of insulin-resistant humans. Studies of oral administration of 9-PAHSA to obese, diabetic mice showed improved glucose tolerance. In characterizing the mechanism, it was found that 9-PAHSA stimulates insulin and GLP-1 secretion and also enhances glucose transport and the Glut4 transporter through activation of GPR-120. 9-PAHSA was also shown to have anti-inflammatory properties.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Mark M Yore et al.
Cell, 159(2), 318-332 (2014-10-11)
Increased adipose tissue lipogenesis is associated with enhanced insulin sensitivity. Mice overexpressing the Glut4 glucose transporter in adipocytes have elevated lipogenesis and increased glucose tolerance despite being obese with elevated circulating fatty acids. Lipidomic analysis of adipose tissue revealed the

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