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SML0256

Sigma-Aldrich

2OHOA

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C18H34O3
Numéro CAS:
56472-29-8
Poids moléculaire :
298.46
Numéro MDL:
MFCD07778553
Code UNSPSC :
12352200
ID de substance PubChem :
329825264
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Conditions de stockage

protect from light

Couleur

white to tan

Solubilité

DMSO: >20 mg/mL

Température de stockage

room temp

Chaîne SMILES 

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-

Clé InChI

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H318

Conseils de prudence

P280 - P305 + P351 + P338

Classification des risques

Eye Dam. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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
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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