SML0256
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:
Molecular Weight:
298.46
MDL number:
UNSPSC Code:
12352200
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
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.
2OHOA is an antitumor agent; sphingomyelin synthase activator.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1
Storage Class Code
11 - Combustible Solids
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
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)
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
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
Nuanyi Liang et al.
Journal of agricultural and food chemistry, 68(32), 8648-8657 (2020-07-17)
The quality of fermented sausage is strongly influenced by its fatty acid (FA). However, the role of a defined starter culture in modifying sausage FA composition, and especially in the production of hydroxy FAs (HFAs), has not been determined. In
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