(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE

Product Name: (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE
CAS No.: 121-40-4
Chemical Name: (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE
Synonyms: TERREIC ACID;(-)-TERREIC ACID;(-)-Terreic acid;5-Dione,3-hydroxy-4;5,6-epoxy-3-hydroxy-p-toluquinone;5,6-epoxy-2-hydroxy-3-methyl-1,4-benzoquinone;2-hydroxy-3-methyl-1,4-benzoquinone5,6-epoxide;(-)-Terreic Acid, Synthetic - CAS 121-40-4 - Calbiochem;3-hydroxy-4-methyl-5-dion(1r)-7-oxabicyclo(4.1.0)hept-3-ene-;(1r)-3-hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
CBNumber: CB1484151
Molecular Formula: C7H6O4
Formula Weight: 154.12
MOL File: 121-40-4.mol

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(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE Property

Melting point:: 127-127.5°
alpha: D22 -16.6° (chloroform); D22 -28.6° (methanol-benzene 1:1); D22 +74.3° (pH 7 phosphate buffer)
Boiling point:: 242.5°C (estimate)
Density: 1.1993 (rough estimate)
refractive index: 1.4300 (estimate)
storage temp.: -20°C
solubility: DMSO: soluble10mg/mL
pka: 4.5(at 25℃)
form: solid
color: White to off-white
LogP: -0.210 (est)

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22
Safety Statements: 36-45
WGK Germany: 3
RTECS: RN8925000
Toxicity: mouse,LD50,intraperitoneal,75mg/kg (75mg/kg),Japanese Journal of Antibiotics. Vol. 33, Pg. 320, 1980.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0480
Product name: Terreic Acid
Purity: from Aspergillus terreus, ≥98% (HPLC)
Packaging: 1mg
Price: $129
Updated: 2024/03/01

Sigma-Aldrich

Product number: 581810
Product name: (-)-Terreic Acid, Synthetic
Packaging: 2mg
Price: $195
Updated: 2023/01/07

Cayman Chemical

Product number: 10010235
Product name: Terreic Acid
Purity: ≥95%
Packaging: 1mg
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 10010235
Product name: Terreic Acid
Purity: ≥95%
Packaging: 5mg
Price: $268
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0480
Product name: Terreic Acid
Purity: from Aspergillus terreus, ≥98% (HPLC)
Packaging: 5mg
Price: $505
Updated: 2024/03/01

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(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE Chemical Properties,Usage,Production

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.

Definition

ChEBI: Terreic acid is a 2-hydroxy-1,4-benzoquinone that is 5,6-epoxy. It is a natural product of Aspergillus terreus. It has an antibacterial activity explained by its inhibitory effect on bacterial enzymes MurA and GlmU. It is an inhibitor of Bruton's tyrosine kinase, and has an anti-tumoral activity against HeLa and EAC cells. It has a role as a mycotoxin, an antibacterial agent, an EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor, an EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor, an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, an Aspergillus metabolite and an antineoplastic agent. It is an arene epoxide, a tertiary alpha-hydroxy ketone, a member of monohydroxy-1,4-benzoquinones and a diketone. It is functionally related to a 2-hydroxy-1,4-benzoquinone.

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.]

(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE Preparation Products And Raw materials

Raw materials

Preparation Products

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(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE Suppliers

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121-40-4, (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONERelated Search:

EC 3.2.1.8 Aspergillus niger ANTIOXIDANT 765 (1β,6β)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione (1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE

(1S,6R)-4-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

(1S,6R)-4-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-quinone

(-)-Terreic Acid, Synthetic - CAS 121-40-4 - Calbiochem

(-)-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

5-Dione,3-hydroxy-4

(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE

5,6-epoxy-2-hydroxy-3-methyl-1,4-benzoquinone

(-)-Terreic acid

7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, (1R,6S)-

121-40-4