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MedKoo Cat#: 461142 | Name: Radicinin

Description:

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

Radicinin is a phytotoxic and antibiotic metabolite produced by some phytopathogenic fungi.

Chemical Structure

Radicinin
Radicinin
CAS#10088-95-6

Theoretical Analysis

MedKoo Cat#: 461142

Name: Radicinin

CAS#: 10088-95-6

Chemical Formula: C12H12O5

Exact Mass: 236.0685

Molecular Weight: 236.22

Elemental Analysis: C, 61.02; H, 5.12; O, 33.86

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 #
No Data
Synonym
Radicinin; Stemphylone;
IUPAC/Chemical Name
(2S,3S)-3-hydroxy-2-methyl-7-((E)-prop-1-en-1-yl)-2,3-dihydro-4H,5H-pyrano[4,3-b]pyran-4,5-dione
InChi Key
SDKXGAICTNHFCN-DCJAWTJCSA-N
InChi Code
InChI=1S/C12H12O5/c1-3-4-7-5-8-9(12(15)17-7)11(14)10(13)6(2)16-8/h3-6,10,13H,1-2H3/b4-3+/t6-,10-/m0/s1
SMILES Code
O=C1[C@@H](O)[C@H](C)Oc(c12)cc(/C=C/C)oc2=O
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 236.22 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: Suzuki M, Sakuno E, Ishihara A, Tamura J, Nakajima H. Conversions of deoxyradicinin to radicinin and of radicinin to 3-epi-radicinin in the phytopathogenic fungus Bipolaris coicis. Phytochemistry. 2012 Mar;75:14-20. doi: 10.1016/j.phytochem.2011.11.010. Epub 2011 Dec 16. PubMed PMID: 22177540. 2: Aldrich TJ, Rolshausen PE, Roper MC, Reader JM, Steinhaus MJ, Rapicavoli J, Vosburg DA, Maloney KN. Radicinin from Cochliobolus sp. inhibits Xylella fastidiosa, the causal agent of Pierce's Disease of grapevine. Phytochemistry. 2015 Aug;116:130-137. doi: 10.1016/j.phytochem.2015.03.015. Epub 2015 Apr 16. PubMed PMID: 25892412. 3: Solfrizzo M, Vitti C, De Girolamo A, Visconti A, Logrieco A, Fanizzi FP. Radicinols and radicinin phytotoxins produced by Alternaria radicina on carrots. J Agric Food Chem. 2004 Jun 2;52(11):3655-60. PubMed PMID: 15161245. 4: Zhang YL, Kong LC, Jiang DH, Yin CP, Cai QM, Chen Q, Zheng JY. Phytotoxic and antifungal metabolites from Curvularia sp. FH01 isolated from the gut of Atractomorpha sinensis. Bioresour Technol. 2011 Feb;102(3):3575-7. doi: 10.1016/j.biortech.2010.10.028. Epub 2010 Oct 13. PubMed PMID: 21035325. 5: Kato K, Hirata Y, Yamamura S. Syntheses of (+ -)-radicinin and (+ -)-dihydroradicinin. J Chem Soc Perkin 1. 1969;15:1997-2002. PubMed PMID: 5387840. 6: Cassone MC. [Electrocardiographic changes induced by various analogs of radicinin]. Boll Soc Ital Biol Sper. 1983 Jan 31;59(1):65-70. Italian. PubMed PMID: 6849694. 7: Kadam S, Poddig J, Humphrey P, Karwowski J, Jackson M, Tennent S, Fung L, Hochlowski J, Rasmussen R, McAlpine J. Citrinin hydrate and radicinin: human rhinovirus 3C-protease inhibitors discovered in a target-directed microbial screen. J Antibiot (Tokyo). 1994 Jul;47(7):836-9. PubMed PMID: 8071130. 8: CLARKE DD, NORD FF. Radicinin: a new pigment from Stemphylium radicinum. Arch Biochem Biophys. 1953 Aug;45(2):469-70. PubMed PMID: 13081157. 9: CLARKE DD, NORD FF. Radicinin: a metabolite from Stemphylium radicinum. I. Chemistry and action. Arch Biochem Biophys. 1955 Nov;59(1):269-84. PubMed PMID: 13269178. 10: Cattel L, Nobili G, Caputo O, Biglino G. [Synthesis of radicinin analogs. I]. Farmaco Sci. 1971 Mar;26(3):247-66. Italian. PubMed PMID: 5102411. 11: Cattel L, Nobili G, Caputo O, Biglino G. [Synthesis of radicinin analogs. II. Reduction of 4H,5H-pyrano-(4,3-b)-pyran-4,5-dione derivatives]. Farmaco Sci. 1971 May;26(5):390-410. Italian. PubMed PMID: 5561444. 12: Cassone MC. [Effects of various radicinin analogs on pulse amplitude and arterial blood pressure]. Boll Soc Ital Biol Sper. 1983 Jan 31;59(1):71-7. Italian. PubMed PMID: 6849695. 13: Solfrizzo M, Girolamo AD, Vitti C, Tylkowska K, Grabarkiewicz-Szczesna J, Szopińska D, Dorna H. Toxigenic profile of Alternaria alternata and Alternaria radicina occurring on umbelliferous plants. Food Addit Contam. 2005 Apr;22(4):302-8. PubMed PMID: 16019799. 14: Biglino G, Cattel L, Nobili G, Caputo O. [Synthesis of analogues and derivatives of radicinin of possible pharmaceutical interest]. Farmaco Sci. 1970 Feb;25(2):145-9. Italian. PubMed PMID: 5453017. 15: Vujcić M, Jankov RM. Microbiologic transformation of progesterone by Curvularia clavata Jain. Steroids. 1990 Jan;55(1):17-21. PubMed PMID: 2309253. 16: Hussain H, Kliche-Spory C, Al-Harrasi A, Al-Rawahi A, Abbas G, Green IR, Schulz B, Krohn K, Shah A. Antimicrobial constituents from three endophytic fungi. Asian Pac J Trop Med. 2014 Sep;7S1:S224-7. doi: 10.1016/S1995-7645(14)60236-4. PubMed PMID: 25312126. 17: Schrader TJ, Cherry W, Soper K, Langlois I, Vijay HM. Examination of Alternaria alternata mutagenicity and effects of nitrosylation using the Ames Salmonella test. Teratog Carcinog Mutagen. 2001;21(4):261-74. PubMed PMID: 11406832. 18: CLARKE DD, NORD FF. Radicinin: a metabolite from Stemphylium radicinum. II. On the mechanism of its biosynthesis. Arch Biochem Biophys. 1955 Nov;59(1):285-93. PubMed PMID: 13269179. 19: Li S, Shao MW, Lu YH, Kong LC, Jiang DH, Zhang YL. Phytotoxic and antibacterial metabolites from Fusarium proliferatum ZS07 isolated from the gut of long-horned grasshoppers. J Agric Food Chem. 2014 Sep 10;62(36):8997-9001. doi: 10.1021/jf502484n. Epub 2014 Aug 28. PubMed PMID: 25146301. 20: Pryor BM, Gilbertson RL. Relationships and taxonomic status of Alternaria radicina, A. carotiincultae, and A. petroselini based upon morphological, biochemical, and molecular characteristics. Mycologia. 2002 Jan-Feb;94(1):49-61. PubMed PMID: 21156477.

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