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(9Z)-12,13-Dihydroxy-9-octadecenoic acid

Names

[ CAS No. ]:
263399-35-5

[ Name ]:
(9Z)-12,13-Dihydroxy-9-octadecenoic acid

[Synonym ]:
cis-12,13-dihydroxy-9-octadecenoic acid
9-Octadecenoic acid, 12,13-dihydroxy-, (9Z)-
Monocrotalin-N-oxid
(9Z)-12,13-Dihydroxy-9-octadecenoic acid
12,13-dihydroxy-9-octadecenoic acid
Monocrotaline,N-oxide

Biological Activity

[Description]:

12,13-DiHOME is a stimulator of Brown adipose tissue (BAT), as well as a thermogenic lipokine that activates BAT in response to cold. (±)12,13-DiHOME activates BAT fuel uptake and enhances cold tolerance, via promoting the translocation of the FA transporters FATP1 and CD36 to the cell membrane. (±)12,13-DiHOME can be used for research of metabolic disorders[1].

[Related Catalog]:

Research Areas >> Metabolic Disease

[In Vivo]

12,13-DiHOME (1 μg/kg;眼球后注射;每天 1 次,共 2 周) 能显著降低小鼠高脂饮食模型中血清甘油三酯水平,并增加 BAT 的摄取以抵御寒冷[1]。 Animal Model: Mice fed a high-fat diet[1] Dosage: 1 μg/kg Administration: Retro-orbitally injection; once daily for 2 weeks Result: Displayed no effects on body weight, glucose tolerance or circulating nonesterified FA. Increased BAT-specific lipid uptake and improved oral lipid tolerance. Increased radiolabeled FA uptake (Fig. 3f) and glucose uptake. Animal Model: To explore the biosynthesis of (±)12, 13-dihome in mice in vivo[1] Dosage: Administration: 7-d cold challenge in mice: mice treated with norepinephrine (NE) for 30 min and exposed to 4°C-cold for 1 h Result: Result: Increased in the circulation of male mice exposed to cold, but not female mice. And also, the enzymes producing 12,13-diHOME were uniquely induced in BAT by cold stimulation.

[References]

[1]. Lynes MD, et al. The cold-induced lipokine 12,13-diHOME promotes fatty acid transport into brown adipose tissue. Nat Med. 2017 May;23(5):631-637.  

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
476.0±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C18H34O4

[ Molecular Weight ]:
314.46

[ Flash Point ]:
255.8±21.1 °C

[ Exact Mass ]:
314.245697

[ PSA ]:
77.76000

[ LogP ]:
4.14

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.493

Synthetic Route

Precursor & DownStream


Related Compounds