Jatrophatrione

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

MedKoo CAT#: 596172

CAS#: 58298-76-3

Description: Jatrophatrione is a bioactive mesotricyclic diterpenoid.


Chemical Structure

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Jatrophatrione
CAS# 58298-76-3

Theoretical Analysis

MedKoo Cat#: 596172
Name: Jatrophatrione
CAS#: 58298-76-3
Chemical Formula: C20H26O3
Exact Mass: 314.1882
Molecular Weight: 314.42
Elemental Analysis: C, 76.40; H, 8.34; O, 15.27

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: Jatrophatrione; NSC 254668; NSC-254668; NSC254668;

IUPAC/Chemical Name: (3aR,9R,10aS,11aS,Z)-3,3,6,9,11a-pentamethyl-2,3,3a,10,10a,11a-hexahydro-1H-dicyclopenta[a,d][9]annulene-1,5,11(4H,9H)-trione

InChi Key: TYBGBKQPLBAYQG-CJIMKZOCSA-N

InChi Code: InChI=1S/C20H26O3/c1-11-6-13-8-12(2)15(21)9-16-19(3,4)10-17(22)20(16,5)18(23)14(13)7-11/h6,8,11,14,16H,7,9-10H2,1-5H3/b12-8-/t11-,14-,16+,20-/m0/s1

SMILES Code: O=C1CC(C)(C)[C@]2([H])[C@]1(C)C([C@]3([H])C(/C=C(C)\C(C2)=O)=C[C@H](C)C3)=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 314.42 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: Melchor-Martínez EM, Silva-Mares DA, Torres-López E, Waksman-Minsky N, Pauli GF, Chen SN, Niemitz M, Sánchez-Castellanos M, Toscano A, Cuevas G, Rivas-Galindo VM. Stereochemistry of a Second Riolozane and Other Diterpenoids from Jatropha dioica. J Nat Prod. 2017 Aug 25;80(8):2252-2262. doi: 10.1021/acs.jnatprod.7b00193. Epub 2017 Aug 3. PubMed PMID: 28771358; PubMed Central PMCID: PMC5714812.

2: Yang J, Long YO, Paquette LA. Concise total syntheses of the bioactive mesotricyclic diterpenoids jatrophatrione and citlalitrione. J Am Chem Soc. 2003 Feb 12;125(6):1567-74. PubMed PMID: 12568617.

3: Paquette LA, Yang J, Long YO. Concerning the antileukemic agent jatrophatrione: the first total synthesis of a [5.9.5] tricyclic diterpene. J Am Chem Soc. 2002 Jun 12;124(23):6542-3. PubMed PMID: 12047168.

4: Paquette LA, Edmondson SD, Monck N, Rogers RD. Studies Directed toward the Synthesis of the Unusual Antileukemic Diterpene Jatrophatrione. 2. Functionalization of Advanced Polycyclic Precursors to the 9-Epi and 8,9-Dehydro Congeners. J Org Chem. 1999 Apr 30;64(9):3255-3265. PubMed PMID: 11674428.

5: Paquette LA, Nakatani S, Zydowsky TM, Edmondson SD, Sun LQ, Skerlj R. Studies Directed toward the Synthesis of the Unusual Antileukemic Diterpene Jatrophatrione. 1. A Solution to the Problem of Chirality Merger during Elaboration of the Entire Carbotricyclic Framework. J Org Chem. 1999 Apr 30;64(9):3244-3254. PubMed PMID: 11674427.

6: Torrance SJ, Wiedhopf RM, Cole JR, Arora SK, Bates RB, Beavers WA, Cutler RS. Antitumor agents from Jatropha macrorhiza (Euphorbiaceae). II. Isolation and characterization of jatrophatrione. J Org Chem. 1976 May 14;41(10):1855-7. PubMed PMID: 1262992.