121-40-4

Basic information

• Product Name: (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE
• Synonyms: (-)-TERREIC ACID;TERREIC ACID;(1r)-3-hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione;2-hydroxy-3-methyl-1,4-benzoquinone5,6-epoxide;3-hydroxy-4-methyl-5-dion(1r)-7-oxabicyclo(4.1.0)hept-3-ene-;5,6-epoxy-3-hydroxy-p-toluquinone;5-dione,3-hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-stereoisomer;(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE
• CAS NO: 121-40-4
• Molecular Formula: C7H6O4
• Molecular Weight: 154.12
• Mol File: 121-40-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 127-127.5°
• Boiling Point: 242.5°C (estimate)
• Flash Point: 147.4 °C
• Appearance: /
• Density: 1.1993 (rough estimate)
• Vapor Pressure: 9.63E-06mmHg at 25°C
• Refractive Index: 1.4300 (estimate)
• Storage Temp.: Store at +4°C
• Solubility: DMSO: soluble10mg/mL
• PKA: 4.5(at 25℃)
• CAS DataBase Reference: (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE(121-40-4)
• EPA Substance Registry System: (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE(121-40-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36-45
• WGK Germany: 3
• RTECS: RN8925000
• Hazardous Substances Data: 121-40-4(Hazardous Substances Data)

Usage

Uses

Terreic Acid is an inhibitor of the catalytic activity of BTK. It is used in the method for treating SWI/SNF complex-deficient cancers comprising glutathione (GSH) metabolic pathway inhibitor.

Hazard

Mycotoxin; poison; mutagen.

Biological Activity

Selective inhibitor of Bruton's tyrosine kinase (BTK). Inhibits the interaction between PKCbII and BTK (IC 50 ~ 30 mM) and the catalytic activity of BTK but does not affect the activity of PKC. Has little effect on the activities of Lyn, Syk, PKA, casein kinase I, ERK1, ERK2 and p38 kinases.

Biochem/physiol Actions

Terreic acid (TA) is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme MurA. The survival of most bacteria depends on the functionality of this cytosolic enzyme. The inactivation of MurA requires the presence of UDP-N-acetylglucosamine 1-Carboxyvinyl transferase, which catalyzes the first step in the biosynthesis of the bacterial cell wall. TA is more potent than the known MurA inhibitor Fosphomycin. TA was also found to severely inhibit the transcription of TNFα and IL-2. TA inhibits protein synthesis by blocking the formation of leucyl-tRNA in sensitive bacteria and inhibits the catalytic effect of Bruton′s tyrosine kinase (Btk), an important factor in B-cell and mast cell activation, by inducing conformational changes that prevent Protein Kinase C (PKC) from interacting with the Btk domain. Moreover, recent studies have demonstrated that TA exhibits a very high level of radical scavenging activity.

Purification Methods

Crystallise terreic acid from *C6H6, *C6H6/pet ether or hexane. Sublime it 80-100o/1mm. [Beilstein 17 IV 6698.]

InChI:InChI=1/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1

Upstream product

• 124175-73-1 2-tert-butoxy-5,6-epoxy-3-methyl-5-(trimethylsilyl)cyclohex-2-ene-1,4-dione 
• 124175-83-3 2-tert-butoxy-3-methyl-5-(trimethylsilyl)cyclohexa-2,5-diene-1,4-dione 
• 124175-84-4 3-tert-butoxy-2-methyl-5-(trimethylsilyl)cyclohexa-2,5-diene-1,4-dione 
• 124175-64-0 2-tert-butoxy-3-methylcyclohexa-2,5-diene-1,4-dione 
• 124175-65-1 2-tert-butoxy-5,6-epoxy-3-methylcyclohex-2-ene-1,4-dione 

Relevant articles and documents

Synthesis of Hydroxyquinones and Related Compounds: Semisquaric Acids, (+/-)-Terreic Acid, (+/-)-Perezone, and (+/-)-Isoperezone

tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature.This is a useful transformation since no reliable general route to hydroxyquinones has previously been available.The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (+/-)-terreic acid, (+/-)-perezone, and (+/-)-isoperezone, are described.