Ascochlorin - >95%, high purity , CAS No.26166-39-2

  • ≥95%
Item Number
A329570
Grouped product items
SKUSizeAvailabilityPrice Qty
A329570-500μg
500μg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$341.90

an inhibitor of matrix metalloproteinase-9 activity

Basic Description

Synonyms3-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)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]benz
Specifications & Purity≥95%
Storage TempStore at -20°C
Shipped InIce chest + Ice pads
Product Description

Ascochlorin is a prenylphenol natural product isolated from the|Ascochyta viciae|fungus that blocks the expression of MMP-9 (matrix metalloproteinase-9) by suppressing activation of the MMP-9 gene. Matrix metalloproteinases are implicated in the behavior of invading and metastatic cells, as these proteins are responsible for modification and degradation of the extracellular matrix. Ascochlorin is shown to blockade the activation of nuclear transcription factor AP-1 (activator protein-1) on the Fra-1 protein, which leads to a suppression of MMP-9 gene expression downstream. This activity is exploited against the growth of MX-1 cells (estrogen receptor-negative cancer cells), where blockade of AP-1 by Ascochlorin provides a crucial cytotoxic handle in the absence of the estrogen receptor chemotherapeutic target. Ascochlorin has also been observed to bind nuclear hormone receptors, and a library of Ascochlorin derivatives showed activity as peroxisome proliferator activated receptor gamma (PPARγ) agonists. Ascochlorin is an activator of p53.

Product Properties

pKapKa: 6.26 (Predicted)

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR2 Tclin Estrogen receptor beta (9272 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1I2 Tchem Pregnane X receptor (6667 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecalis (29875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C3H 10T1/2 (488 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ascobolus (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name 5-chloro-2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde
INCHI InChI=1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m1/s1
InChi Key SETVRSKZJJWOPA-FLDGXQSCSA-N
Canonical SMILES CC1CCC(=O)C(C1(C)C=CC(=CCC2=C(C(=C(C(=C2O)Cl)C)C=O)O)C)C
Isomeric SMILES C[C@@H]1CCC(=O)[C@@H]([C@@]1(C)/C=C/C(=C/CC2=C(C(=C(C(=C2O)Cl)C)C=O)O)/C)C
WGK Germany 3
RTECS VH3707560
PubChem CID 11258227
Molecular Weight 404.93

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Chemical and Physical Properties

SolubilitySoluble in ethanol, methanol, DMF, DMSO (0.9-1.1 mg/ml), chloroform, and ethyl acetate. Insoluble in water.
Refractive Indexn20D1.60 (Predicted)
Boil Point(°C)556.91° C at 760 mmHg (Predicted)
Melt Point(°C)226.87° C (Predicted)

Safety and Hazards(GHS)

WGK Germany 3
RTECS VH3707560
RIDADR NONHforallmodesoftransport

Related Documents

Solution Calculators