ChemicalBook > CAS DataBase List > (1R,6S)-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

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

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


  • (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