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441816 (-)-Ascofuranone CAS: 38462-04-3

Specifications
References
CAS Number
38462-04-3
Grade
Highly Purified
Molecular Formula
C23H29ClO5
Molecular Weight
420.93
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadien-1-yl]benzaldehyde;|[S-(E,E)]-3-Chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl]-benzaldehyde; Ascofuranone

Ascofuranone is an isoprenoid antibiotic originally isolated as a hypolipidemic substance from the phytopathogenic fungus, Ascochyta viciae by researchers at Chugai Pharmaceutical Co., Japan in 1973. Ascofuranone demonstrates antitumor activity against FM3A murine mammary, B16 melanoma and Lewis lung carcinomas. Ascofuranone increases splenic cytotoxicity and phagocytic activity of host animal cells. Ascofuranone targets c-Myc independent of p53. Ascofuranone also inhibits respiration, mitochondrial uptake and glycerol-3-phosphate dehydrogenase. Ascofuranone is active against trypanosomes.

Synonyms
3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadien-1-yl]benzaldehyde; [S-(E,E)]-3-Chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl]-benzaldehyde; Ascofuranone
CAS No
38462-04-3
Molecular Formula
C23H29ClO5
Molecular Weight
420.93
Appearance
As reported
Purity
≥95% (HPLC)
Melting Point
xxx°C
Solubility
Soluble in Ethanol, Methanol, DMF or DMSO.
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
1. Isolation and structure of ascofuranone and asofuranol, antibiotics with hypolipidemic activity. Sasaki H. et al. J Antibiot 1973, 26, 676|2. Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes. Magae J. et al. J Antibiot 1988, XLI, 959|3. p53-independent induction of G1 arrest and p21WAF1/CIP1 expression by ascofuranone, an isoprenoid antibiotic, through downregulation of c-Myc. Jeong J-H. Mol Cancer Ther 2010, 9, 2102.|4. Yabu, Y., et al.: Parasitol. Int., 52, 155 (2003)|5. Cho, H., et al.: Carcinogenesis, 28, 1104 (2007)
USBio References
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