13S-hydroxyoctadecadienoic acid

Names

[ Name ]:
13S-hydroxyoctadecadienoic acid

[Synonym ]:
(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid
13-Hydroxy-9c,11t-octadecadienoic acid
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid
13(S)-HYDROXYOCTADECA-9Z,11E-DIENOIC ACID
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid
9,11-Octadecadienoic acid, 13-hydroxy-, (9Z,11E,13S)-
13(S)-HODE

Biological Activity

[Description]:

(S)-Coriolic acid (13(S)-HODE), the product of 15-lipoxygenase (15-LOX) metabolism of linoleic acid, functions as the endogenous ligand to activate PPARγ. (S)-Coriolic acid is an important intracellular signal agent and is involved in cell proliferation and differentiation in various biological systems. (S)-Coriolic acid induces mitochondrial dysfunction and airway epithelial injury[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Research Areas >> Inflammation/Immunology

[In Vitro]

(S)-Coriolic acid (25μM) causes mitochondrial structural alterations and injury in bronchial epithelium[2]. (S)-Coriolic acid (30 nM; 6 hours; E-FABP-/- keratinocytes) induces K1 expression through NF-κB activation. (S)-Coriolic acid increases the phosphorylation of IκBαat serine 32, which induces IκB degradation and thereby activates NF-κB. (S)-Coriolic acid also increases the phosphorylation of Ikkinase-bat tyrosine 199, which promotes IκBα phosphorylation and subsequent NF-kB activation[3].

[In Vivo]

(S)-Coriolic acid (0-0.6 mg per mouse; Intranasally once a day for 3 consecutive days) causes severe airway dysfunction, airway neutrophilia, mitochondrial dysfunction and epithelial injury[2]. Animal Model: BALB/c mice (6-8 weeks)[2] Dosage: 0-0.6 mg per mouse Administration: Intranasally once a day for 3 consecutive days Result: BALB/c mice developed features of mitochondrial dysfunction such as reduction in mitochondrial membrane potential, reduction in complex IV activity in lung mitochondria, and increase in the levels of cytochrome c in lung cytosol.

[References]

[1]. Yuan H, et al. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. Thorax. 2010;65(4):321-326.

[2]. Mabalirajan U, et al. Linoleic acid metabolite drives severe asthma by causing airway epithelial injury. Sci Rep. 2013;3:1349.

[3]. Ogawa E, et al. Epidermal FABP (FABP5) regulates keratinocyte differentiation by 13(S)-HODE-mediated activation of the NF-κB signaling pathway. J Invest Dermatol. 2011;131(3):604-612.

[4]. Yuan H, et al. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. Thorax. 2010;65(4):321-326.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
422.7±20.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₃₂O₃

[ Molecular Weight ]:
296.445

[ Flash Point ]:
223.6±18.3 °C

[ Exact Mass ]:
296.235138

[ PSA ]:
57.53000

[ LogP ]:
5.32

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.492

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ Hazard Codes ]:
F: Flammable;

[ Risk Phrases ]:
11

[ RIDADR ]:
UN 1170 3/PG 2

[ HS Code ]:
2918199090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918199090

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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