SML0256

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: 56472-29-8
• Molecular Weight: 298.46
• MDL number: MFCD07778553
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825264
• NACRES: NA.77

Properties

• 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

Description

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

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.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H318
• Precautionary Statements: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable