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(11R,12S)-(5Z,7E,9E,14Z)-11,12-dihydroxy-5,7,9,14-eicosatetraenoic acid, also referred to as (11R,12S)-diHETE, is a lipoxygenase-derived eicosanoid metabolite characterized by a conjugated tetraene system and vicinal diol stereocenters at C11 and C12. Its synthesis has been achieved through stereoselective approaches, including the use of sugar-derived chiral templates and Wittig reactions for carbon framework assembly, as well as epoxide ring-opening strategies to introduce the diol functionality. (11R,12S)-(5Z,7E,9E,14Z)-11,12-dihydroxy-5,7,9,14-eicosatetraenoic acid is of interest due to its structural complexity and potential biological relevance as a lipid mediator. Other names for (11R,12S)-(5Z,7E,9E,14Z)-11,12-dihydroxy-5,7,9,14-eicosatetraenoic acid include: - (11R,12S)-dihydroxyeicosa-5Z,7E,9E,14Z-tetraenoic acid - (11R,12S)-diHETE - 11R,12S-dihydroxy-5Z,7E,9E,14Z-eicosatetraenoic acid

117857-80-4

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117857-80-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 117857-80-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,8,5 and 7 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 117857-80:
(8*1)+(7*1)+(6*7)+(5*8)+(4*5)+(3*7)+(2*8)+(1*0)=154
154 % 10 = 4
So 117857-80-4 is a valid CAS Registry Number.

117857-80-4Downstream Products

117857-80-4Relevant academic research and scientific papers

Stereoselective synthesis of (11R, 12S)-(5Z,7E,9E,14Z)-11, 12-dihydroxy-5,7,9,14-eicosatetraenoic acid from 'Diacetone Glucose'

Sharma,Rao, S. Mahender

, p. 4231 - 4232 (1994)

A stereoselective total synthesis of (11R,12S)-diHETE is described. The strategy is based on the use of a 'sugar' derived 'chiron' for the incorporation of vic-diol' stereocentres, while Wittig reactions for the assembly of requisite carbon frame work of the target molecule.

Epoxide ring opening of α,β-epoxysilanes with prop-2-ynyl sulfide dianion - Synthesis of (11R,12S,5Z,7E,9E,14Z)-dihydroxyeicosa-5,7,9,14-tetraenoic acid

Kobayashi, Yuichi,Shimizu, Kiyoshi,Sato, Fumie

, p. 493 - 494 (1997)

A new methodology for synthesis of lipoxygenase metabolites possessing vic-diol substructures coupled with the conjugated alkene system is developed and successfully applied to the synthesis of (11R,12S,5Z,7E,9E,14Z)-dihydroxyeicosa-5,7,9,14-tetraenoic ac

Total synthesis of (5R,6S)-, (5S,6S)- and (11R,12S)- DIHETEs from tricarbonyl(η4-butadienyl) iron(0) complexes.

Lellouche, J. P.,Gigou-Barbedette, A.,Gree, R.

, p. 605 - 624 (2007/10/02)

The total synthesis of (5R,6S)-, (5S,6S)-, and (11R,12S)-DIHETEs are described starting from the two chiral tricarbonyl (η4-butadienyl)iron complexes (-)-(2R,5S)-12 and (+)-(2S,5R)-13.This new synthetic approach shows an efficient use of these

TOTAL SYNTHESIS OF (11R,12S)-diHETE

Gigou, Agnes,Beaucourt, Jean-Pierre,Lellouche, Jean-Paul,Gree, Rene

, p. 635 - 638 (2007/10/02)

The first total synthesis of (11R,12S) diHETE is reported.The key step is the highly chemio- and stereoselective osmylation of a double bond in a trienyne system selectively complexed by an Fe(CO)3 group.

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