Jimenezin

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

MedKoo CAT#: 596230

CAS#: 204185-17-1

Description: 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

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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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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

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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.