94161-10-1

Basic information

• Product Name: 10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID
• Synonyms: 10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID;HEPOXILIN B3;(5Z,8Z)-10-hydroxy-10-[(2S,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid;(5Z,8Z,14Z)-10-Hydroxy-11,12-epoxy-5,8,14-icosatrienoic acid;10,11(12)-HEPETRE
• CAS NO: 94161-10-1
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• Mol File: 94161-10-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 503.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.046±0.06 g/cm3(Predicted)
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: 10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID(94161-10-1)
• EPA Substance Registry System: 10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID(94161-10-1)

Safety Data

• Hazardous Substances Data: 94161-10-1(Hazardous Substances Data)

Usage

Description

10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID, also known as Hepoxilin B, is a major eicosanoid produced in the human epidermis. It is a bioactive lipid mediator that plays a crucial role in various physiological and pathological processes, including inflammation, cell signaling, and tissue repair.

Uses

Used in Pharmaceutical Industry:
10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID is used as a therapeutic agent for the treatment of inflammatory skin conditions, such as psoriasis. It is incorporated onto phospholipids in psoriatic lesions of human epidermis fragments and epidermal cells, helping to regulate the immune response and reduce inflammation.
Used in Cosmetic Industry:
10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID is used as an active ingredient in anti-aging and skin repair formulations. Its ability to modulate cell signaling and promote tissue repair makes it a valuable component in skincare products designed to improve skin health and appearance.
Used in Research:
10(R,S)-HYDROXY-11(S),12(S)-TRANS-EPOXYEICOSA-5Z,8Z,14Z-TRIENOIC ACID is used as a research tool to study the role of eicosanoids in various biological processes. Its unique structure and bioactivity make it an important compound for investigating the mechanisms of inflammation, cell signaling, and other physiological processes.

Upstream product

• 160080-78-4 (5Z,8Z)-(S)-10-(4-Methoxy-benzyloxy)-10-[(2S,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-deca-5,8-dienoic acid methyl ester 
• 160017-28-7 (5Z,8Z)-(S)-10-[(4R,5R)-2,2-Dimethyl-5-((Z)-oct-2-enyl)-[1,3]dioxolan-4-yl]-10-(4-methoxy-benzyloxy)-deca-5,8-dienoic acid methyl ester 
• 160017-29-8 (5Z,8Z,14Z)-(10S,11R,12R)-11,12-Dihydroxy-10-(4-methoxy-benzyloxy)-icosa-5,8,14-trienoic acid methyl ester 
• 160017-25-4 (3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 160017-27-6 (S)-2-[(4R,5R)-2,2-Dimethyl-5-((Z)-oct-2-enyl)-[1,3]dioxolan-4-yl]-2-(4-methoxy-benzyloxy)-ethanol 
• 160080-76-2 (3aR,7S,7aS)-7-Hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 16666-79-8 hexylidenetriphenylphosphoran 
• 160080-79-5 10(S),11(R),12(R)-hepoxilin B₃ methyl ester 
• 173522-75-3 Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2S,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester 
• 160080-80-8 10(R),11(R),12(R)-hepoxilin B₃ methyl ester 
• 127902-30-1 (2R,3S)-2,3-Epoxyundec-5-yn-1-al 
• 151592-80-2 (2S,3S)-1-Hydroxy-2,3-epoxyundec-5-yne 
• 75290-52-7 1-hydroxyundeca-2(E)-en-5-yne 
• 77758-51-1 methyl hex-5-ynoate 

Relevant articles and documents

Synthesis, properties, and identification of epimeric hepoxilins (-)-(10R)-B3 and (+)-(10S)-B3

To characterize the individual epimers of hepoxilin B3, a new total synthesis procedure was developed consisting of subsequent condensations of enentiomerically pure (2R,3S)-epoxy-5-undecynal with LiC≡CCH2Cl and HC≡C(CH2)3COOMe, followed by Lindlar hydrogenation, and finally epimer separation. Derivatives of hepoxilin syn-(10R,11R,12S)-B3 (free acid, methyl ester and acetate of methyl ester) are more polar on silica gel, have negative optical rotations [α]25D -60.6°, -62.6°, -25.2°, respectively, and in 1H NMR spectra have the larger splitting of carbinolic H-10 signal (J10,11 5.0-6.1 Hz). Corresponding values for less polar hepoxilin anti-(10S, 11R,12S)-B3 derivatives are: [α]25D +73.5°, +61.9°, and -2.0°; J10-11 2.95-3.3 Hz. These data suggest that an epimer of hepoxilin B3 recently isolated by W.H.Gerwick et al. from red algae is syn-(10R,11R,12S)-B3.

Hepoxilins B3: Synthesis of all four stereoisomers and a glutathione adduct

Utilizing (-)-quinic acid as a differentiated bis-aldehyde chiron, both pairs of hepoxilin B3 enantiomers and a glutathione adduct were synthesized by regiospecific functionalization of an acyclic vic-diol.