12S-HHTrE

Names

[ Name ]:
12S-HHTrE

[Synonym ]:
5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (5Z,8E,10E,12S)-
12(s)-hht
12S-HHTrE
(5Z,8E,10E,12S)-12-Hydroxy-5,8,10-heptadecatrienoic acid

Biological Activity

[Description]:

12S-HHT (12(S)-HHTrE) is an enzymatic product of prostaglandin H2 (PGH2) derived from cyclooxygenase (COX)-mediated arachidonic acid metabolism. 12S-HHT is an endogenous ligand for BLT2 that fully activates BLT2 in vivo. 12S-HHT suppresses UV-induced IL-6 synthesis in keratinocytes, exerting an anti-inflammatory activity[1][2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Leukotriene Receptor

Research Areas >> Inflammation/Immunology

[In Vitro]

12S-HHT (0-150 nM; 3 hours) has anti-inflammatory activity by attenuating the UVB-induced IL-6 synthesis in HaCaT cells[2]. 12S-HHT inhibits the UVB-stimulated p38 MAPK/NF-κB pathway by up-regulating MKP-1, which leads to the suppression of IL-6 synthesis[2].12S-HHT is an endogenous agonist for BLT2[3]. Western Blot Analysis[2] Cell Line: HaCaT cells Concentration: 0, 12.5, 25, 75 or 150 nM Incubation Time: 3 hours Result: UVB (5 mJ/cm2) irradiation markedly up-regulated IL-6 synthesis and release, which was suppressed by the treatment with 12-HHT in a concentration-dependent manner.

[References]

[1]. Saeki K, et al. Identification, signaling, and functions of LTB4 receptors. Semin Immunol. 2017;33:30-36.

[2]. Lee JW, et al. 12(S)-Hydroxyheptadeca-5Z,8E,10E-trienoic acid suppresses UV-induced IL-6 synthesis in keratinocytes, exerting an anti-inflammatory activity. Exp Mol Med. 2012;44(6):378-386.

[3]. Okuno T, et al. Metabolism and biological functions of 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid. Prostaglandins Other Lipid Mediat. 2021;152:106502.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
451.8±45.0 °C at 760 mmHg

[ Melting Point ]:
151.79 (Mean or Weighted MP)ºC

[ Molecular Formula ]:
C₁₇H₂₈O₃

[ Molecular Weight ]:
280.402

[ Flash Point ]:
241.1±25.2 °C

[ Exact Mass ]:
280.203857

[ PSA ]:
57.53000

[ LogP ]:
4.30

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.507

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
F: Flammable;Xi: Irritant;

[ Risk Phrases ]:
R11

[ Safety Phrases ]:
16-26-36

[ RIDADR ]:
UN 1170 3

[ HS Code ]:
2918199090

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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Related Compounds

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