ascochlorin

Product Name: ascochlorin
CAS No.: 26166-39-2
Chemical Name: ascochlorin
Synonyms: Nsc 287492;ascochlorin;Ilicicolin D;Ll-Z 1272 gamma;Antibiotics LL-Z 1272g;Antibiotic ll-Z1272 gamma;LL-Z 1272 gaMMa, Ilicicolin D;beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (E,E)-;5-Chloro-2,4-dihydroxy-6-methyl-3-[(2E,4Z)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde;3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R)-1β,2β,6β-trimethyl-3-oxocyclohexyl]-2,4-pentadienyl]benzaldehyde
CBNumber: CB01364846
Molecular Formula: C23H29ClO4
Formula Weight: 404.931
MOL File: 26166-39-2.mol

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ascochlorin Property

Melting point:: 172-174 °C
Boiling point:: 556.9±39.0 °C(Predicted)
Density: 1.199±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMSO: soluble
pka: 6.26±0.50(Predicted)
form: A powder

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Safety

WGK Germany: 3
Toxicity: mouse,LD50,intraperitoneal,20mg/kg (20mg/kg),Journal of Antibiotics. Vol. 21, Pg. 539, 1968.

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 19437
Product name: Ascochlorin
Purity: ≥98%
Packaging: 500μg
Price: $288
Updated: 2024/03/01

Cayman Chemical

Product number: 19437
Product name: Ascochlorin
Purity: ≥98%
Packaging: 2.5mg
Price: $1147
Updated: 2024/03/01

TRC

Product number: A787028
Product name: Ascochlorin
Packaging: 2.5mg
Price: $3150
Updated: 2021/12/16

Usbiological

Product number: A3690
Product name: Ascochlorin
Packaging: 500ug
Price: $523
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0025816
Product name: ASCOCHLORIN
Purity: 95.00%
Packaging: 0.5MG
Price: $549
Updated: 2021/12/16

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ascochlorin Chemical Properties,Usage,Production

Uses

Ascochlorin is an antitumor fungal metabolite which specifically inhibits matrix metalloproteinase-9 (MMP-9) activity through suppression of activator protein-1 (AP-1)-dependent induction of MMP-9 gene expression. Via AP-1 suppression, ascochlorin selectively kills MX-1 cells, a human breast cancer cell line lacking estrogen receptors. Ascochlorin also shows activity against Newcastle disease and herpes simplex viruses.

Uses

Ascochlorin is an isoprenoid antibiotic and antiviral that has diverse effects on mammalian cells. It suppresses PMA-induced invasion in renal carcinoma cells (IC50 = ~10 μM) by inhibiting the expression of matrix metalloproteinase-9. At 2 μM, ascochlorin profoundly increases the expression of p53 by increasing protein stability in cancer cells, and, at 50 μm, it inhibits signaling through STAT3. Ascochlorin also binds and inhibits the mitochondrial cytochrome bc1 complex, blocking reduction of cytochrome b by ubiquinone.[Cayman Chemical]

Definition

ChEBI: Ascochlorin is a dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (1E,3E)-3-methyl-1-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-1,3-dien-5-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by several fungi including Ascochyta viciae. It exhibits anticancer, antifungal and antiprotozoal activities. It has a role as an antineoplastic agent, a fungal metabolite, an antifungal agent, an antiprotozoal drug and an angiogenesis inhibitor. It is a dihydroxybenzaldehyde, a member of monochlorobenzenes, an olefinic compound, a member of resorcinols, a meroterpenoid, a sesquiterpenoid and a member of cyclohexanones. It is a conjugate acid of an ascochlorin(1-).

ascochlorin Preparation Products And Raw materials

Raw materials

Preparation Products

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ascochlorin Suppliers

China 20 India 1 United Kingdom 1 United States 8 Global 30

BOC Sciences

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ProdList: 19741
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TargetMol Chemicals Inc.

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ProdList: 32165
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TargetMol Chemicals Inc.

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Aladdin Scientific

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ProdList: 52925
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Cayman Chemical Company

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United States Biological

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MedChemExpress

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Riedel-de Haen AG

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26166-39-2, ascochlorinRelated Search:

LF163892 MONOHYDRATE A-1331852 5-METHYL-2-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-1,3-BENZENEDIOL 2-ALLYL-6-CHLOROPHENOL ILICICOLIN F ascochlorin

3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R)-1β,2β,6β-trimethyl-3-oxocyclohexyl]-2,4-pentadienyl]benzaldehyde

Ilicicolin D

3-Chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)benzaldehyde (1R-(1alpha(2E,4E),2beta,6beta))-

Antibiotic ll-Z1272 gamma

ascochlorin

Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (1R-(1alpha(2E,4E),2beta,6beta))-

beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (E,E)-

Ll-Z 1272 gamma

Nsc 287492

LL-Z 1272 gaMMa, Ilicicolin D

5-Chloro-2,4-dihydroxy-6-methyl-3-[(2E,4Z)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde

Antibiotics LL-Z 1272g

Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]-2,4-pentadien-1-yl]-

26166-39-2