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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

BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19743
Advantage
58
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
19892
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
52927
Advantage
58

26166-39-2, ascochlorinRelated Search:


  • 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