CAS Number87-11-6
SynonymsN-(4-Methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide; N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-acetamide; 6-(Acetylamino)-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one; 6-Acetamido-4-methyl-1,2-dithiolo<4,3-b>pyrrol-5(4H)-on; 6-Acetamido-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one; 6-(Acetamido)-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one; MFCD07370147; 3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole; Thiolutin; N-(4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-acetamid; 3-Acetamido-5-methylpyrrolin-4-one(4,3-d)-1,2-dithiole; 6-acetylamino-4-methyl-4H-[1,2]dithiolo[4,3-b]pyrrol-5-one
Molecular FormulaC8H8N2O2S2
Molecular Weight228.29
Purity≥95 (HPLC)%
Density1.6±0.1 g/cm3
Boiling Point478.6±45.0 °C at 760 mmHg
Melting Point273-276℃
Appearancesolid
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 87-11-6 |
| Catalog No. | 2A-1177774 |
| Chinese Name | 硫藤黄素 |
| Synonyms | N-(4-Methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide; N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-acetamide; 6-(Acetylamino)-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one; 6-Acetamido-4-methyl-1,2-dithiolo<4,3-b>pyrrol-5(4H)-on; 6-Acetamido-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one; 6-(Acetamido)-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one; MFCD07370147; 3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole; Thiolutin; N-(4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-acetamid; 3-Acetamido-5-methylpyrrolin-4-one(4,3-d)-1,2-dithiole; 6-acetylamino-4-methyl-4H-[1,2]dithiolo[4,3-b]pyrrol-5-one |
| Molecular Formula | C8H8N2O2S2 |
| Molecular Weight | 228.29 |
| Purity | ≥95 (HPLC) |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 478.6±45.0 °C at 760 mmHg |
| Melting Point | 273-276℃ |
| Appearance | solid |
| Water Solubility | DMSO: 5 mg/mL |
| Storage Condition | Warehouse ventilation and low temperature drying |
| Application | Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-vascular compound produced by Streptomyces. Thiolutin inhibits the JAB1/MPN/Mov34 (JAMM) metalloprotease Csn5, a SHAM-Domain-of |
| HTC | 2933990090 |
| PubChem ID | 329826766 |
| MDL Number | MFCD07370147 |
| SMILES | CCC(=O)NC1=C2SSC=C2N(C)C1=O |
| InChI | 1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12) |
| InChI Key | UGZYFXMSMFMTSM-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352105 |
| MSDS | msds/178371_1_87_11_6.pdf |
| Use of | Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-angiogenic compound produced by Streptomyces. Thiolutin inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36[1]. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation[2]. Properties Articles27 Name N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide Synonym More Synonyms Thiolutin Biological Activity Description Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-angiogenic compound produced by Streptomyces. Thiolutin inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36[1]. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation[2]. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Metabolic Disease References [1]. Lauinger L, et al. Thiolutin is a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases. Nat Chem Biol. 2017 Jul;13(7):709-714. [2]. Jia Y, et al. Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton. Cell Stress Chaperones. 2010 Mar;15(2):165-81. Chemical & Physical Properties Molecular Formula C8H8N2O2S2 Exact Mass 228.002716 PSA 107.58000 Index of Refraction 1.721 InChIKey MHMRAFONCSQAIA-UHFFFAOYSA-N Toxicological Information CHEMICAL IDENTIFICATION RTECS NUMBER : CHEMICAL NAME : 1,2-Dithiolo(4.3-b)pyrrol-5(4H)-one, 6-acetamido-4-methyl- CAS REGISTRY NUMBER : BEILSTEIN REFERENCE NO. : LAST UPDATED : DATA ITEMS CITED : MOLECULAR FORMULA : C8-H8-N2-O2-S2 MOLECULAR WEIGHT : WISWESSER LINE NOTATION : T55 BNV FSSJ B1 DMV1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value MUTATION DATA TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Yeast - Saccharomyces cerevisiae DOSE/DURATION : REFERENCE : AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 3,729,1973 Safety Information Signal Word Danger Hazard Statements H300 Precautionary Statements P264-P301 + P310 Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges Hazard Codes T+: Very toxic;T: Toxic; Risk Phrases 28 Safety Phrases S45 WGK Germany 3 RTECS JP1355000 HS Code 2933990090 Synthetic Route Methyl-6-acetam... 139102-08-2 Literature: Stachel, Hans-Dietrich; Nienaber, Juliane; Zoukas, Thomas Liebigs Annalen der Chemie, 1992 , # 5 p. 473 - 480 N-(5,6-Dihydro-... 142705-66-6 Literature: Stachel, Hans-Dietrich; Nienaber, Juliane; Zoukas, Thomas Liebigs Annalen der Chemie, 1992 , # 5 p. 473 - 480 Methyl-4,5-dihy... 139101-74-9 Literature: Liebigs Annalen der Chemie, , # 5 p. 473 - 480 Precursor & DownStream Precursor 7 CAS#:139102-08-2 Methyl-6-acetam... CAS#:142705-66-6 N-(5,6-Dihydro-... CAS#:139101-74-9 Methyl-4,5-dihy... CAS#:139101-96-5 5-Methyl-2,2-di... DownStream 0 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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