(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 Structure](CAS/GIF/121-40-4.gif)
- 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
- Molecular Weight:
- 154.12
- MDL Number:
- MFCD01710762
- MOL File:
- 121-40-4.mol
| 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 |
| LogP | -0.210 (est) |
| FDA UNII | XM2Y0DRJ7D |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H312-H302 | |||||||||
| Precautionary statements | P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501 | |||||||||
| 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. | |||||||||
| NFPA 704 |
|
(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE price More Price(12)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML0480 | Terreic Acid from Aspergillus terreus, ≥98% (HPLC) | 121-40-4 | 1mg | $129 | 2024-03-01 | Buy |
| Sigma-Aldrich | 581810 | (-)-Terreic Acid, Synthetic | 121-40-4 | 2mg | $195 | 2023-01-07 | Buy |
| Cayman Chemical | 10010235 | Terreic Acid ≥95% | 121-40-4 | 1mg | $68 | 2024-03-01 | Buy |
| Cayman Chemical | 10010235 | Terreic Acid ≥95% | 121-40-4 | 5mg | $268 | 2024-03-01 | Buy |
| Sigma-Aldrich | SML0480 | Terreic Acid from Aspergillus terreus, ≥98% (HPLC) | 121-40-4 | 5mg | $505 | 2024-03-01 | Buy |
(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE Chemical Properties,Uses,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
(1R,6S)-3-HYDROXY-4-METHYL-7-OXABICYCLO[4.1.0]HEPT-3-ENE-2,5-DIONE Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Career Henan Chemica Co | +86-0371-86658258 15093356674; | laboratory@coreychem.com | China | 30255 | 58 |
| BOC Sciences | +16314854226 | inquiry@bocsci.com | United States | 19743 | 58 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 821-50328103-801 18930552037 | 3bsc@sina.com | China | 15848 | 69 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51471 | 80 |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8449 | 60 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9709 | 58 |
| BOC Sciences | -- | info@bocsci.com | USA | 0 | 65 |
| ChemeGen(Shanghai) Biotechnology Co.,Ltd. | 18818260767 | sales@chemegen.com | China | 11289 | 58 |
| Meng Cheng Technology (Shanghai) Co., LTD | 400-820-6829 | sales@mitachieve.com | China | 8864 | 58 |
| Energy Chemical | 021-58432009 400-005-6266 | marketing1@energy-chemical.com | China | 44894 | 58 |