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MedKoo Cat#: 584546 | Name: Ascochlorin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ascochlorin is an isoprenoid antibiotic that is produced by the phytopathogenic fungus Ascochyta viciae.

Chemical Structure

Ascochlorin
Ascochlorin
CAS#26166-39-2

Theoretical Analysis

MedKoo Cat#: 584546

Name: Ascochlorin

CAS#: 26166-39-2

Chemical Formula: C23H29ClO4

Exact Mass: 404.1754

Molecular Weight: 404.93

Elemental Analysis: C, 68.22; H, 7.22; Cl, 8.75; O, 15.80

Price and Availability

Size Price Availability Quantity
500µg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Ascochlorin; (-)-Ascochlorin; Ilicicolin D; LL-Z 1272 gamma; Antibiotic LL-Z1272γ; NSC 287492; NSC287492; NSC-287492;
IUPAC/Chemical Name
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))-
InChi Key
SETVRSKZJJWOPA-FLDGXQSCSA-N
InChi Code
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
SMILES Code
O=CC1=C(O)C(C/C=C(C)/C=C/[C@]2(C)[C@@H](C)C(CC[C@H]2C)=O)=C(O)C(Cl)=C1C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 404.93 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Isaka M, Yangchum A, Supothina S, Laksanacharoen P, Jennifer Luangsa-Ard J, Hywel-Jones NL. Ascochlorin derivatives from the leafhopper pathogenic fungus Microcera sp. BCC 17074. J Antibiot (Tokyo). 2015 Jan;68(1):47-51. doi: 10.1038/ja.2014.90. Epub 2014 Jul 2. PubMed PMID: 24984794. 2: Dai X, Ahn KS, Kim C, Siveen KS, Ong TH, Shanmugam MK, Li F, Shi J, Kumar AP, Wang LZ, Goh BC, Magae J, Hui KM, Sethi G. Ascochlorin, an isoprenoid antibiotic inhibits growth and invasion of hepatocellular carcinoma by targeting STAT3 signaling cascade through the induction of PIAS3. Mol Oncol. 2015 Apr;9(4):818-33. doi: 10.1016/j.molonc.2014.12.008. Epub 2015 Jan 5. PubMed PMID: 25624051; PubMed Central PMCID: PMC5528777. 3: Lee SH, Kwak CH, Lee SK, Ha SH, Park J, Chung TW, Ha KT, Suh SJ, Chang YC, Chang HW, Lee YC, Kang BS, Magae J, Kim CH. Anti-Inflammatory Effect of Ascochlorin in LPS-Stimulated RAW 264.7 Macrophage Cells Is Accompanied With the Down-Regulation of iNOS, COX-2 and Proinflammatory Cytokines Through NF-κB, ERK1/2, and p38 Signaling Pathway. J Cell Biochem. 2016 Apr;117(4):978-87. doi: 10.1002/jcb.25383. Epub 2016 Feb 5. PubMed PMID: 26399466. 4: Kawaguchi M, Fukuda T, Uchida R, Nonaka K, Masuma R, Tomoda H. A new ascochlorin derivative from Cylindrocarpon sp. FKI-4602. J Antibiot (Tokyo). 2013 Jan;66(1):23-9. doi: 10.1038/ja.2012.75. Epub 2012 Nov 21. PubMed PMID: 23168404. 5: Jeong JH, Jeong YJ, Cho HJ, Shin JM, Kang JH, Park KK, Park YY, Chung IK, Chang HW, Magae J. Ascochlorin inhibits growth factor-induced HIF-1α activation and tumor-angiogenesis through the suppression of EGFR/ERK/p70S6K signaling pathway in human cervical carcinoma cells. J Cell Biochem. 2012 Apr;113(4):1302-13. doi: 10.1002/jcb.24001. PubMed PMID: 22109717. 6: Cho HJ, Kang JH, Jeong JH, Jeong YJ, Park KK, Park YY, Moon YS, Kim HT, Chung IK, Kim CH, Chang HW, Chang YC. Ascochlorin suppresses TGF-β1-induced PAI-1 expression through the inhibition of phospho-EGFR in rat kidney fibroblast cells. Mol Biol Rep. 2012 Apr;39(4):4597-603. doi: 10.1007/s11033-011-1251-y. Epub 2011 Sep 23. PubMed PMID: 21947785. 7: Shin JM, Jeong YJ, Cho HJ, Magae J, Bae YS, Chang YC. Suppression of c-Myc induces apoptosis via an AMPK/mTOR-dependent pathway by 4-O-methyl-ascochlorin in leukemia cells. Apoptosis. 2016 May;21(5):657-68. doi: 10.1007/s10495-016-1228-3. Erratum in: Apoptosis. 2016 May;21(5):669-70. PubMed PMID: 26922069. 8: Jeong JH, Kang JH, Hwang SL, Cho HJ, Park KK, Park YY, Chung IK, Chang HW, Kim CH, Min KS, Kim HD, Magae J, Kang SS, Chang YC. 4-O-methylascochlorin, methylated derivative of ascochlorin, stabilizes HIF-1α via AMPK activation. Biochem Biophys Res Commun. 2011 Mar 18;406(3):353-8. doi: 10.1016/j.bbrc.2011.02.043. Epub 2011 Feb 15. PubMed PMID: 21329651. 9: Berry EA, Huang LS, Lee DW, Daldal F, Nagai K, Minagawa N. Ascochlorin is a novel, specific inhibitor of the mitochondrial cytochrome bc1 complex. Biochim Biophys Acta. 2010 Mar;1797(3):360-70. doi: 10.1016/j.bbabio.2009.12.003. Epub 2009 Dec 16. PubMed PMID: 20025846; PubMed Central PMCID: PMC2819552. 10: Dai X, Ahn KS, Wang LZ, Kim C, Deivasigamni A, Arfuso F, Um JY, Kumar AP, Chang YC, Kumar D, Kundu GC, Magae J, Goh BC, Hui KM, Sethi G. Ascochlorin Enhances the Sensitivity of Doxorubicin Leading to the Reversal of Epithelial-to-Mesenchymal Transition in Hepatocellular Carcinoma. Mol Cancer Ther. 2016 Dec;15(12):2966-2976. Epub 2016 Oct 7. PubMed PMID: 27765853. 11: Jeong JH, Nakajima H, Magae J, Furukawa C, Taki K, Otsuka K, Tomita M, Lee IS, Kim CH, Chang HW, Min KS, Park KK, Park KK, Chang YC. Ascochlorin activates p53 in a manner distinct from DNA damaging agents. Int J Cancer. 2009 Jun 15;124(12):2797-803. doi: 10.1002/ijc.24259. PubMed PMID: 19253369. 12: Kang JH, Chang YC, Maurizi MR. 4-O-carboxymethyl ascochlorin causes ER stress and induced autophagy in human hepatocellular carcinoma cells. J Biol Chem. 2012 May 4;287(19):15661-71. doi: 10.1074/jbc.M112.358473. Epub 2012 Mar 20. PubMed PMID: 22433868; PubMed Central PMCID: PMC3346088. 13: Jeong JH, Chang YC. Ascochlorin, an isoprenoid antibiotic, induces G1 arrest via downregulation of c-Myc in a p53-independent manner. Biochem Biophys Res Commun. 2010 Jul 16;398(1):68-73. doi: 10.1016/j.bbrc.2010.06.037. Epub 2010 Jun 15. PubMed PMID: 20558137. 14: Kang JH, Park KK, Lee IS, Magae J, Ando K, Kim CH, Chang YC. Proteome analysis of responses to ascochlorin in a human osteosarcoma cell line by 2-D gel electrophoresis and MALDI-TOF MS. J Proteome Res. 2006 Oct;5(10):2620-31. PubMed PMID: 17022633. 15: Hosono K, Ogihara J, Ohdake T, Masuda S. LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae. J Antibiot (Tokyo). 2009 Oct;62(10):571-4. doi: 10.1038/ja.2009.80. Epub 2009 Aug 14. PubMed PMID: 19680284. 16: Seephonkai P, Isaka M, Kittakoop P, Boonudomlap U, Thebtaranonth Y. A novel ascochlorin glycoside from the insect pathogenic fungus Verticillium hemipterigenum BCC 2370. J Antibiot (Tokyo). 2004 Jan;57(1):10-6. PubMed PMID: 15032480. 17: Hong S, Park KK, Magae J, Ando K, Lee TS, Kwon TK, Kwak JY, Kim CH, Chang YC. Ascochlorin inhibits matrix metalloproteinase-9 expression by suppressing activator protein-1-mediated gene expression through the ERK1/2 signaling pathway: inhibitory effects of ascochlorin on the invasion of renal carcinoma cells. J Biol Chem. 2005 Jul 1;280(26):25202-9. Epub 2005 Apr 29. PubMed PMID: 15863510. 18: Shin JM, Jeong YJ, Cho HJ, Magae J, Bae YS, Chang YC. Erratum to: Suppression of c-Myc induces apoptosis via an AMPK/mTOR-dependent pathway by 4-O-methyl-ascochlorin in leukemia cells. Apoptosis. 2016 May;21(5):669-70. doi: 10.1007/s10495-016-1239-0. PubMed PMID: 27030036. 19: Togashi M, Ozawa S, Abe S, Nishimura T, Tsuruga M, Ando K, Tamura G, Kuwahara S, Ubukata M, Magae J. Ascochlorin derivatives as ligands for nuclear hormone receptors. J Med Chem. 2003 Sep 11;46(19):4113-23. PubMed PMID: 12954063. 20: Tsuruga M, Nakajima H, Ozawa S, Togashi M, Chang YC, Ando K, Magae J. Characterization of 4-O-methyl-ascochlorin-induced apoptosis in comparison with typical apoptotic inducers in human leukemia cell lines. Apoptosis. 2004 Jul;9(4):429-35. PubMed PMID: 15192325.