54397-85-2

Basic information

• Product Name: THROMBOXANE B2
• Synonyms: THROMBOXANE B2;TXB2;9ALPHA,11,15S-TRIHYDROXYTHROMBA-5Z,13E-DIEN-1-OIC ACID;[5Z,9ALPHA,11RS,13E,15S]-9,11,15-TRIHYDROXYTHROMBOXA-5,13-DIEN-1-OIC ACID;(5z,9α,11rs,13e,15s)-9,11,15-trihydroxythromboxa-5,13-dien-1-oic acid;(E)-7-[(2S,3S,4S)-4,6-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]oxan-3-yl]hept-5-enoic acid;TXB2, (5Z,9α,11RS,13E,15S)-9,11,15-Trihydroxythromboxa-5,13-dien-1-oic acid;(5Z,13E,15S)-9α,11,15-Trihydroxythromboxa-5,13-dien-1-oic acid
• CAS NO: 54397-85-2
• Molecular Formula: C₂₀H₃₄O₆
• Molecular Weight: 370.48
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 54397-85-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 95-96°
• Boiling Point: 582.5 °C at 760 mmHg
• Flash Point: 199.7 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 5.38E-16mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly, Heated)
• Merck: 13,9466
• CAS DataBase Reference: THROMBOXANE B2(CAS DataBase Reference)
• NIST Chemistry Reference: THROMBOXANE B2(54397-85-2)
• EPA Substance Registry System: THROMBOXANE B2(54397-85-2)

Safety Data

• Hazard Codes: Xn,T
• Statements: 63-52/53-34-32-23/24/25-5
• Safety Statements: 22-36-45-36/37/39-26
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 54397-85-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 54397-85-2 differently. You can refer to the following data:
1. An inactive metabolite/product of Thromboxane A2 (TBXA2): a compound involved in platelet activation and aggregation in case of a wound. Urinary analysis of TXB2 accurately reflects intrarenal TXA2 synthesis while measurement of 11-dehydro TBX2 (D230555) and 2,3-dinor thromboxane metabolites gives the best estimate of systemic TXA2 secretion.
2. TXB2 is a stable, biologically inert metabolite formed from the non-enzymatic hydrolysis of TXA2, which has a half-life of about 30 seconds. Urinary analysis of TXB2 accurately reflects intrarenal TXA2 synthesis, while measurement of 11-dehydro and 2,3-dinor thromboxane metabolites gives the best estimate of systemic TXA2 secretion.

Definition

ChEBI: A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.

InChI:InChI=1/C20H34O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,20-22,25H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4-,13-12+/t15-,16-,17-,18+,20?/m0/s1

Upstream product

• 61684-24-0 (Z)-7-[(2S,3R,4R)-4-Hydroxy-2-((E)-3-hydroxy-oct-1-enyl)-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid 
• 73176-48-4 thromboxane B₂ methyl glycoside 
• 186664-08-4 (3aR,4S,6S,7S,7aR)-4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxy)-ethyl]-7-iodo-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 186664-09-5 (3aS,4S,6S,7aS)-4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 186664-12-0 (3aS,4S,6S,7aS)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-oct-2-enyl]-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 186664-11-9 (R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde 
• 186664-10-8 (3aS,4S,6S,7aS)-4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 186664-07-3 (3aR,4S,6S,7S,7aR)-4-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-7-iodo-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 186664-06-2 2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide 
• 186664-15-3 Acetic acid (E)-(S)-1-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-oct-2-enyl ester 

Downstream Products

• 136181-24-3 C₂₆H₄₀O₉ 
• 105449-97-6 diethylhydrogensilyl-cyclic diethylsilylene derivative of thromboxane B₂ methyl ester-methyloxime (anti isomer) 
• 105449-97-6 diethylhydrogensilyl-cyclic diethylsilylene derivative of thromboxane B₂ methyl ester-methyloxime (syn isomer) 

Relevant articles and documents

Total Synthesis of Thromboxane B2via a Key Bicyclic Enal Intermediate

A 12-step asymmetric synthesis of thromboxane B2 (TxB2) from 2,5-dimethoxytetrahydrofuran is described. The synthesis employs our organocatalytic aldol reaction of succinaldehyde to give a key bicyclic enal intermediate. From here, the synthetic strategy involves a conjugate addition of an alkenyl side chain to the bicyclic enal, Baeyer-Villiger oxidation, and a highly Z-selective Wittig olefination of a hemiacetal. Key to success was minimizing redox operations and the manipulation of functional groups in the correct order.

Enzyme-catalyzed synthesis of eicosanoids in organic solvents

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Total synthesis of thromboxane B2 starting from (R,R)-tartaric acid as a chiral pool

Optically active natural thromboxane B2 (TXB2) was synthesized from (R,R)-tartaric acid as only chiral source. The synthesis was achieved through regio- and stereoselective introduction of acetate moiety at the C2-position of the 6,8-dioxabicyclo[3.2.1]octene derivative (2) to provide an acetamide derivative (6), partial ring opening of 6 to give a pyranoid (10), and construction of the C15-hydroxyl group of TXB2 by stereospecific allylic transposition of the inherent chirality of tartaric acid in the transallylic acetate (18).