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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

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About This Item

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

Quality Level

100

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

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
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Karolina Węder et al.
Biochimica et biophysica acta. Biomembranes, 1860(11), 2329-2336 (2018-06-05)
2-Hydroxyoleic acid (2OHOA, Minerval), a derivative of oleic acid, is the lipid used in Membrane Lipid Therapy. This compound is of confirmed anticancer effect, however its exact mechanism of action has not been fully elucidated. In this work the interactions
Maria Laura Martin et al.
Journal of lipid research, 54(5), 1457-1465 (2013-03-09)
The mechanism of action of 2-hydroxyoleic acid (2OHOA), a potent antitumor drug, involves the rapid and specific activation of sphingomyelin synthase (SMS), leading to a 4-fold increase in SM mass in tumor cells. In the present study, we investigated the
Amaia Marcilla-Etxenike et al.
PloS one, 7(10), e48235-e48235 (2012-11-08)
2-Hydroxyoleic acid is a synthetic fatty acid with potent anti-cancer activity which does not induce undesired side effects. However, the molecular and cellular mechanisms by which this compound selectively kills human glioma cancer cells without killing normal cells is not
The influence of 2-hydroxyoleic acid--an anticancer drug--on model membranes of different fluidity modulated by the cholesterol content
Olechowska K, et al.
Journal of Molecular Liquids, 283, 756-762 (2019)
Virginia L Bass et al.
Lipids in health and disease, 19(1), 128-128 (2020-06-09)
Inhalation of common air pollutants such as diesel and biodiesel combustion products can induce vascular changes in humans which may contribute to increased mortality and morbidity associated with fine particulate matter exposures. Diesel, biodiesel, and other combustion byproducts contain fatty
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