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SML0256

Sigma-Aldrich

2OHOA

≥98% (HPLC)

Sinonimo/i:

(9Z)-2-Hydroxy-9-octadecenoic acid; cis-2-Hydroxy-9-octadecenoic acid, 2-Hydroxy Oleic Acid, Minerval

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About This Item

Formula empirica (notazione di Hill):
C18H34O3
Numero CAS:
56472-29-8
Peso molecolare:
298.46
Numero MDL:
MFCD07778553
Codice UNSPSC:
12352200
ID PubChem:
329825264
NACRES:
NA.77

Saggio

≥98% (HPLC)

Condizioni di stoccaggio

protect from light

Colore

white to tan

Solubilità

DMSO: >20 mg/mL

Temperatura di conservazione

room temp

Stringa SMILE

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-
JBSOOFITVPOOSY-KTKRTIGZSA-N

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H318

Consigli di prudenza

P280 - P305 + P351 + P338

Classi di pericolo

Eye Dam. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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
Eun-Ji Jang et al.
Drug delivery, 24(1), 1587-1597 (2017-10-17)
Studies have shown that insertion of oleic acid into lipid bilayers can modulate the membrane properties of liposomes so as to improve their function as drug carriers. Considering that 2-hydroxyoleic acid (2OHOA), a potential antitumor agent currently undergoing clinical trials
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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