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H7021

Sigma-Aldrich

2-Hydroxyhexadecanoic acid

≥98% (capillary GC)

Synonym(s):

2-Hydroxypalmitic acid, DL-α-Hydroxypalmitic acid

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About This Item

Linear Formula:
CH3(CH2)13CH(OH)COOH
CAS Number:
764-67-0
Molecular Weight:
272.42
EC Number:
212-129-1
MDL number:
MFCD00014343
UNSPSC Code:
12352211
PubChem Substance ID:
24895781
NACRES:
NA.25

Quality Level

200

Assay

≥98% (capillary GC)

lipid type

saturated FAs

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCCCC(O)C(O)=O

InChI

1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15,17H,2-14H2,1H3,(H,18,19)

InChI key

JGHSBPIZNUXPLA-UHFFFAOYSA-N

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Biochem/physiol Actions

2-Hydroxyhexadecanoic acid (2OH-HDA) is used as a representative of the saturated long-chain hydroxyl fatty acids group, members of which have potential roles in anti-inflammatory action, neuroprotection, and bactericide and anti-cancer defense.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Elena E Pohl et al.
Biochimica et biophysica acta, 1778(5), 1292-1297 (2008-03-04)
Hydroxyl group-containing fatty acids play an important role in anti-inflammatory action, neuroprotection, bactericide and anti-cancer defense. However, the mechanism of long-chain hydroxy fatty acids (HFA) transport across plasma membranes is still disputed. Two main hypotheses have been suggested: firstly, that
Tomotake Morita et al.
Bioscience, biotechnology, and biochemistry, 75(8), 1597-1599 (2011-08-09)
Cryptococcus humicola JCM 1461 efficiently produced cellobiose lipids (CLs), bolaform biosurfactants. The main product was identified as 16-O-(2″,3″,4″,6'-tetra-O-acetyl-β-cellobiosyl)-2-hydroxyhexadecanoic acid. The production yield of CLs reached 13.1 g/L under the intermittent feeding of glucose. The critical micelle concentrations (CMC) of the
B D Beaumelle et al.
Molecular and biochemical parasitology, 28(1), 39-42 (1988-02-01)
The intraerythrocytic malaria parasite depends on the surrounding medium for a supply of phospholipid precursors. Efficient inhibition (IC50 7-90 microM) of Plasmodium falciparum growth in vitro was achieved using modified fatty acids. The fatty acid analogues most effective in suppressing
N Takakuwa et al.
Bioresource technology, 96(9), 1089-1092 (2005-01-26)
Glucosylceramides were surveyed in crop tissues and by-products from their processing. Apple pulp contained the highest amount (0.94 mg g(-1)) of glucosylceramide and relatively less sterylglucoside, which is the major contaminant of partially purified glucosylceramide. Glucosylceramide from apple pulp was
K M Koshy et al.
Chemistry and physics of lipids, 34(1), 41-53 (1983-12-01)
Chromatographically pure galactosylceramide I3-sulfate (cerebroside sulfate (CBS)) containing palmitic acid or D-2-hydroxypalmitic acid has been prepared by the acylation of galactosylsphingosine I3-sulfate obtained from the saponification of bovine brain sulfatides. Optically pure D-2-hydroxypalmitic acid was obtained by adapting literature methods
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