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

Description

THROMBOXANE B2, also known as TXB2, is a member of the thromboxanes B class, specifically identified as (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11, and 15. It is a white solid and serves as an inactive metabolite/product of Thromboxane A2 (TBXA2), which plays a crucial role in platelet activation and aggregation during wound healing.

Uses

Used in Medical Diagnostics:
THROMBOXANE B2 is used as a biomarker for assessing intrarenal TXA2 synthesis and systemic TXA2 secretion. The urinary analysis of TXB2 provides an accurate reflection of intrarenal TXA2 synthesis, while the measurement of 11-dehydro and 2,3-dinor thromboxane metabolites offers the best estimate of systemic TXA2 secretion. This application is particularly relevant in the medical industry for diagnosing and monitoring various conditions related to blood clotting and platelet function.
Used in Research and Development:
In the pharmaceutical and biotechnology industries, THROMBOXANE B2 serves as a valuable compound for research and development purposes. Its role in platelet activation and aggregation makes it an important target for the development of new drugs and therapies aimed at treating conditions related to blood clotting disorders, such as thrombosis and hemorrhage. Additionally, its use in understanding the underlying mechanisms of TXA2 synthesis and secretion can contribute to the advancement of medical knowledge and the development of novel treatment strategies.

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

• 62210-97-3 (Z)-7-[(2R,3S,4S,6S)-4-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 186664-13-1 (3aS,4S,6S,7aS)-4-((E)-(S)-1-Hydroxy-oct-2-enyl)-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 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 
• 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 
• 186664-07-3 (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 
• 186664-10-8 (3aS,4S,6S,7aS)-4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one 
• 186664-11-9 (R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde 
• 186664-12-0 (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 
• 186664-09-5 (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 
• 186664-08-4 (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 
• 73176-48-4 thromboxane B₂ methyl glycoside 

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).