13S-hydroxyoctadecadienoic acid

Modify Date: 2024-01-12 11:32:19

13S-hydroxyoctadecadienoic acid Structure
13S-hydroxyoctadecadienoic acid structure
Common Name 13S-hydroxyoctadecadienoic acid
CAS Number 29623-28-7 Molecular Weight 296.445
Density 1.0±0.1 g/cm3 Boiling Point 422.7±20.0 °C at 760 mmHg
Molecular Formula C18H32O3 Melting Point N/A
MSDS USA Flash Point 223.6±18.3 °C
Symbol GHS02 GHS07
GHS02, GHS07
Signal Word Danger

 Use of 13S-hydroxyoctadecadienoic acid


(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].

 Names

Name 13(s)-hode
Synonym More Synonyms

 13S-hydroxyoctadecadienoic acid 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
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

 Safety Information

Symbol GHS02 GHS07
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  0

DownStream  1

 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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 Synonyms

(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