MedKoo Cat#: 558479 | Name: Botryodiplodin

Description:

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

Botryodiplodin is an antibiotic with antileukemic activity isolated from Botryodiplodia theobromae. It has an interesting property of turning the skin of the individual various shades of pink 2-3 hrs after application. It is a toxic metabolite of Penicillium carneo-lutescens.

Chemical Structure

Botryodiplodin
Botryodiplodin
CAS#27098-03-9

Theoretical Analysis

MedKoo Cat#: 558479

Name: Botryodiplodin

CAS#: 27098-03-9

Chemical Formula: C7H12O3

Exact Mass: 144.0800

Molecular Weight: 144.17

Elemental Analysis: C, 58.32; H, 8.39; O, 33.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Botryodiplodin; Cytostipin; Antibiotic PSX 1;
IUPAC/Chemical Name
2-Hydroxy-3-methyl-4-acetyltetrahydrofuran
InChi Key
CLYSZQBIUYRLNX-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H12O3/c1-4-6(5(2)8)3-10-7(4)9/h4,6-7,9H,3H2,1-2H3
SMILES Code
O=C(C1C(C)C(O)OC1)C
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 144.17 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: Moulé Y, Renauld F, Darracq N. Repair of DNA-protein cross-links induced by the mycotoxin botryodiplodin in mammalian cells. Carcinogenesis. 1984 Jul;5(7):907-10. PubMed PMID: 6733851. 2: Moulé Y, Renauld F, Darracq N, Douce C. DNA-protein cross-linking by the mycotoxin, botryodiplodin, in mammalian cells. Carcinogenesis. 1982;3(2):211-4. PubMed PMID: 7067047. 3: Fuska J, Proksa B, Uhrín D. The antibiotic PSX-1 produced by Penicillium stipitatum is identical with botryodiplodin. Folia Microbiol (Praha). 1988;33(3):238-40. PubMed PMID: 3397011. 4: Moulé Y, Douce C, Moreau S, Darracq N. Effects of the mycotoxin botryodiplodin on mammalian cells in culture. Chem Biol Interact. 1981 Oct;37(1-2):155-64. PubMed PMID: 7285241. 5: Ramezani M, Shier WT, Abbas HK, Tonos JL, Baird RE, Sciumbato GL. Soybean charcoal rot disease fungus Macrophomina phaseolina in Mississippi produces the phytotoxin (-)-botryodiplodin but no detectable phaseolinone. J Nat Prod. 2007 Jan;70(1):128-9. PubMed PMID: 17253865. 6: Mioso R, Toledo Marante FJ, Herrera Bravo de Laguna I. Penicillium roqueforti: a multifunctional cell factory of high value-added molecules. J Appl Microbiol. 2015 Apr;118(4):781-91. doi: 10.1111/jam.12706. Epub 2014 Dec 29. Review. PubMed PMID: 25421646. 7: Moulé Y, Decloitre F, Hamon G. Mutagenicity of the mycotoxin botryodiplodin in the Salmonella typhimurium/microsomal activation test. Environ Mutagen. 1981;3(3):287-91. PubMed PMID: 7023925. 8: Moulé Y, Darracq N. Absence of DNA breaks during repair of DNA-protein cross-links induced by the mycotoxin botryodiplodin in mammalian cells. Carcinogenesis. 1984 Oct;5(10):1375-7. PubMed PMID: 6488460. 9: Andolfi A, Maddau L, Cimmino A, Linaldeddu BT, Basso S, Deidda A, Serra S, Evidente A. Lasiojasmonates A-C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen. Phytochemistry. 2014 Jul;103:145-153. doi: 10.1016/j.phytochem.2014.03.016. Epub 2014 Apr 23. PubMed PMID: 24768282. 10: Douce C, Moreau S, Decloitre F, Moulé Y. Relationships between the biological effects and chemical structure of the genotoxic mycotoxin, botryodiplodin. Carcinogenesis. 1982;3(5):587-8. PubMed PMID: 7046982. 11: San Gupta R, Chandran RR, Divekar PV. Botryodiplodin--a new antibiotic from Botryodiplodia theobromae. II. Production, isolation and biological properties. Indian J Exp Biol. 1966 Jul;4(3):152-3. PubMed PMID: 5969953. 12: Cabedo N, López-Gresa MP, Primo J, Ciavatta ML, González-Mas MC. Isolation and structural elucidation of eight new related analogues of the mycotoxin (-)-botryodiplodin from Penicillium coalescens. J Agric Food Chem. 2007 Aug 22;55(17):6977-83. Epub 2007 Jul 12. PubMed PMID: 17628075. 13: McCurry PM Jr, Abe K. Stereochemistry and synthesis of the antileukemic agent botryodiplodin. J Am Chem Soc. 1973 Aug 22;95(17):5824-5. PubMed PMID: 4733827. 14: Zang Y, Genta-Jouve G, Retailleau P, Escargueil A, Mann S, Nay B, Prado S. Talaroketals A and B, unusual bis(oxaphenalenone) spiro and fused ketals from the soil fungus Talaromyces stipitatus ATCC 10500. Org Biomol Chem. 2016 Mar 7;14(9):2691-7. doi: 10.1039/c5ob02657a. PubMed PMID: 26837531. 15: Fujimoto Y, Kamiya M, Tsunoda H, Ohtsubo K, Tatsuno T. [Toxicological study on the metabolites of Penicillium carneo-lutescens]. Chem Pharm Bull (Tokyo). 1980;28(4):1062-6. French. PubMed PMID: 7418105. 16: Horáková L, Nouza K, Pospísil M, Konopásková E, Klapácová J, Fuska J. Immunosuppressive properties of the antibiotics cytostipin and vermiculine. Folia Biol (Praha). 1980;26(5):312-26. PubMed PMID: 7002636. 17: Daub GW, Edwards JP, Okada CR, Allen JW, Maxey CT, Wells MS, Goldstein AS, Dibley MJ, Wang CJ, Ostercamp DP, Chung S, Cunningham PS, Berliner MA. Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement. J Org Chem. 1997 Apr 4;62(7):1976-1985. PubMed PMID: 11671499.