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MedKoo Cat#: 464633 | Name: Ipomeamarone

Description:

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

Ipomeamarone is a natural toxic furanoterpenoid found in mold-damaged sweet potatoes.

Chemical Structure

Ipomeamarone
Ipomeamarone
CAS#20007-82-3 (racemic)

Theoretical Analysis

MedKoo Cat#: 464633

Name: Ipomeamarone

CAS#: 20007-82-3 (racemic)

Chemical Formula: C15H22O3

Exact Mass: 250.1569

Molecular Weight: 250.34

Elemental Analysis: C, 71.97; H, 8.86; O, 19.17

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 #
494-23-5 (RS-isomer) 20007-82-3 (racemic)
Synonym
Ipomeamarone; Ngaione; BOHLMANN 176; BOHLMANN-176;
IUPAC/Chemical Name
1-(5-(furan-3-yl)-2-methyltetrahydrofuran-2-yl)-4-methylpentan-2-one
InChi Key
WOFDWNOSFDVCDF-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H22O3/c1-11(2)8-13(16)9-15(3)6-4-14(18-15)12-5-7-17-10-12/h5,7,10-11,14H,4,6,8-9H2,1-3H3
SMILES Code
CC(C)CC(CC1(C)OC(C2=COC=C2)CC1)=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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 250.34 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: Dowa Y, Yamada Y, Kato M, Matsumoto N, Kama Y, Shiihara T. Sweet Potato Was Not So Sweet: Undetected Foreign-body Aspiration in a Healthy Child Leading to Acute Bronchial Asthma. Tokai J Exp Clin Med. 2019 Apr 20;44(1):1-4. PMID: 30963521. 2: Wamalwa LN, Cheseto X, Ouna E, Kaplan F, Maniania NK, Machuka J, Torto B, Ghislain M. Toxic Ipomeamarone accumulation in healthy parts of Sweetpotato (Ipomoea batatas L. Lam) storage roots upon infection by Rhizopus stolonifer. J Agric Food Chem. 2015 Jan 14;63(1):335-42. doi: 10.1021/jf504702z. PMID: 25418792; PMCID: PMC4298358. 3: Nemoto H. Synthetic organic chemistry based on small ring compounds. Chem Pharm Bull (Tokyo). 2007 Jul;55(7):961-74. doi: 10.1248/cpb.55.961. PMID: 17603183. 4: Shi Q, Tan X, Mao Z, Tao N, Yi Y. [Study of ceratocystis fimbriata toxins determination from sweet potato by high performance thin-layer chromatography]. Wei Sheng Yan Jiu. 2003 Jul;32(4):381-3. Chinese. PMID: 14535108. 5: Jenett-Siems K, Siems K, Witte L, Eich E. Merrekentrones A-D, ipomeamarone- like furanosesquiterpenes from Merremia kentrocaulos. J Nat Prod. 2001 Nov;64(11):1471-3. doi: 10.1021/np010233j. PMID: 11720538. 6: Raposo JB, Mendez MC, Riet-Correa F, de Andrade GB. Experimental intoxication by Myoporum laetum in sheep. Vet Hum Toxicol. 1998 Jun;40(3):132-5. PMID: 9610488. 7: Shen Y. [Determination of furanoterpenoid toxins from sweet potato by thin- layer chromatography]. Se Pu. 1997 Jul;15(4):328-30. Chinese. PMID: 15739468. 8: Makino T, Kato K, Iyozumi H, Honzawa H, Tachiiri Y, Hiramatsu M. Ultraweak luminescence generated by sweet potato and Fusarium oxysporum interactions associated with a defense response. Photochem Photobiol. 1996 Dec;64(6):953-6. doi: 10.1111/j.1751-1097.1996.tb01860.x. PMID: 8972637. 9: Fujita M, Oba K, Uritani I. Properties of a Mixed Function Oxygenase Catalyzing Ipomeamarone 15-Hydroxylation in Microsomes from Cut-Injured and Ceratocystis fimbriata-Infected Sweet Potato Root Tissues. Plant Physiol. 1982 Aug;70(2):573-8. doi: 10.1104/pp.70.2.573. PMID: 16662536; PMCID: PMC1067190. 10: Lee JS, Hrdlicka J, Seawright AA. The effect of daily oral dosing with ngaione for 7 weeks on the liver of the rat. J Appl Toxicol. 1981 Jun;1(3):165-73. doi: 10.1002/jat.2550010307. PMID: 6821080. 11: Lee JS, Hrdlicka J, Seawright AA. The effect of size and timing of a pretreatment dose of phenobarbitone on the liver lesion caused by ngaione in the mouse. J Pathol. 1979 Mar;127(3):121-7. doi: 10.1002/path.1711270304. PMID: 469637. 12: Scott PM. Mycotoxins in Feeds and Ingredients and their Origin. J Food Prot. 1978 May;41(5):385-398. doi: 10.4315/0362-028X-41.5.385. PMID: 30795147. 13: Catalano EA, Hasling VC, Dupuy HP, Constantin RJ. Ipomeamarone in blemished and diseased sweet potatoes (Ipomea batatas). J Agric Food Chem. 1976 Jan- Feb;25(1):94-6. doi: 10.1021/jf60209a041. PMID: 1002943. 14: Wood G, Huang A. The detection and quantitative determination of ipomeamarone in damaged sweet potatoes (Ipomoea batatas). J Agric Food Chem. 1975 Mar-Apr;23(2):239-41. doi: 10.1021/jf60198a017. PMID: 1133296. 15: Coxon DT, Curtis RF, Howard B. Ipomeamarone, a toxic furanoterpenoid in sweet potatoes (Ipomea batatas) in the United Kingdom. Food Cosmet Toxicol. 1975 Feb;13(1):87-90. doi: 10.1016/0015-6264(75)90086-3. PMID: 1123206. 16: Burka LT, Wilson BJ, Harris TM. A synthesis of racemic ipomeamarone and epiipomeamarone. J Org Chem. 1974 Jul 26;39(15):2212-4. doi: 10.1021/jo00929a015. PMID: 4850340. 17: Oguni I. Dehydroipomeamarone as an Intermediate in the Biosynthesis of Ipomeamarone, a Phytoalexin from Sweet Potato Root Infected with Ceratocystis fimbriata. Plant Physiol. 1974 Apr;53(4):649-52. doi: 10.1104/pp.53.4.649. PMID: 16658760; PMCID: PMC541414. 18: AKAZAWA T. BIOSYNTHESIS OF IPOMEAMARONE. II. SYNTHETIC MECHANISM. Arch Biochem Biophys. 1964 Jun;105:512-6. doi: 10.1016/0003-9861(64)90044-x. PMID: 14236635. 19: AKAZAWA T, URITANI I, AKAZAWA Y. Biosynthesis of ipomeamarone. I. The incorporation of acetate-2-C14 and mevalonate-2-C14 into ipomeamarone. Arch Biochem Biophys. 1962 Oct;99:52-9. doi: 10.1016/0003-9861(62)90242-4. PMID: 14011505. 20: Akazawa T, Wada K. Analytical study of ipomeamarone & chlorogenic acid alterations in sweet potato roots infected by Ceratocystis fimbriata. Plant Physiol. 1961 Mar;36(2):139-44. doi: 10.1104/pp.36.2.139. PMID: 16655482; PMCID: PMC406108.

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MDVN1003

MDVN1003