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SML0256

Sigma-Aldrich

2OHOA

≥98% (HPLC)

Synonym(s):
(9Z)-2-Hydroxy-9-octadecenoic acid; cis-2-Hydroxy-9-octadecenoic acid, 2-Hydroxy Oleic Acid, Minerval
Empirical Formula (Hill Notation):
C18H34O3
CAS Number:
Molecular Weight:
298.46
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

storage condition

protect from light

color

white to tan

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

CCCCCCCC\C=C/CCCCCCC(O)C(O)=O

InChI

1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/b10-9-

InChI key

JBSOOFITVPOOSY-KTKRTIGZSA-N

Application

2OHOA has been used as:
  • a modulator of the sphingolipid and glycerophospholipid pathway to study its effects on myelination in mice Charcot–Marie–Tooth type 1A (CMT1A) myelinopathy and myelinating dorsal root ganglia cultures
  • in biophysical studies to study its effects on artificial membranes
  • to study its interactions with major membrane lipid films

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

2-Hydroxy oleic acid (2OHOA) is a derivative of oleic acid. It plays a role in membrane organization, alterations in membrane fluidity, an increase of the tendency to form non-lamellar structures, and remodeling of microdomains by interacting with the lipids in membranes of pathological cells.
2OHOA induces cell cycle arrest and apoptosis in several cancer cell lines, including glioma, leukemia, breast and colon cancer lines. 2OHOA increases sphingomyelin (SM) levels in the membranes of tumor cells, which typically display decreased SM membrane content, and remodeled membranes, compared with normal cells. The compound has no effect on SM levels in non-cancer cells.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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Quotes and Ordering

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