MedKoo Cat#: 596230 | Name: Jimenezin

Description:

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

Jimenezin is a member of the class of compounds known as annonaceous acetogenins. Annonaceous acetogenins are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Jimenezin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Jimenezin can be found in alcoholic beverages and fruits, which makes jimenezin a potential biomarker for the consumption of these food products. Jimenezin is found in alcoholic beverages. Jimenezin is a constituent of the seeds of Rollinia mucosa (biriba).

Chemical Structure

Jimenezin
Jimenezin
CAS#204185-17-1

Theoretical Analysis

MedKoo Cat#: 596230

Name: Jimenezin

CAS#: 204185-17-1

Chemical Formula: C37H66O7

Exact Mass: 622.4809

Molecular Weight: 622.92

Elemental Analysis: C, 71.34; H, 10.68; O, 17.98

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
Jimenezin;
IUPAC/Chemical Name
(S)-3-((2R,13R)-13-((2R,5R)-5-((2S,5R,6S)-6-decyl-5-hydroxytetrahydro-2H-pyran-2-yl)tetrahydrofuran-2-yl)-2,13-dihydroxytridecyl)-5-methylfuran-2(5H)-one
InChi Key
MAHVNJPZHYFHHE-IMEDPYHGSA-N
InChi Code
InChI=1S/C37H66O7/c1-3-4-5-6-7-12-15-18-21-33-32(40)22-23-35(43-33)36-25-24-34(44-36)31(39)20-17-14-11-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31+,32+,33-,34+,35-,36+/m0/s1
SMILES Code
O=C1O[C@@H](C)C=C1C[C@H](O)CCCCCCCCCC[C@H]([C@@H]2O[C@@H]([C@@H]3CC[C@@H](O)[C@H](CCCCCCCCCC)O3)CC2)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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 622.92 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: Matsui Y, Takeuchi T, Kumamoto-Yonezawa Y, Takemura M, Sugawara F, Yoshida H, Mizushina Y. The relationship between the molecular structure of natural acetogenins and their inhibitory activities which affect DNA polymerase, DNA topoisomerase and human cancer cell growth. Exp Ther Med. 2010 Jan;1(1):19-26. Epub 2010 Jan 1. PubMed PMID: 23136587; PubMed Central PMCID: PMC3490394. 2: Takahashi S, Yonezawa Y, Kubota A, Ogawa N, Maeda K, Koshino H, Nakata T, Yoshida H, Mizushina Y. Pyranicin, a non-classical annonaceous acetogenin, is a potent inhibitor of DNA polymerase, topoisomerase and human cancer cell growth. Int J Oncol. 2008 Feb;32(2):451-8. PubMed PMID: 18202768. 3: Bandur NG, Brückner D, Hoffmann RW, Koert U. Total synthesis of jimenezin via an intramolecular allylboration. Org Lett. 2006 Aug 17;8(17):3829-31. PubMed PMID: 16898828. 4: Takahashi S, Maeda K, Hirota S, Nakata T. Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure. Org Lett. 1999 Dec 16;1(12):2025-8. PubMed PMID: 10905863.