Jacaranone

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

MedKoo CAT#: 596093

CAS#: 60263-07-2

Description: Jacaranone is a cytotoxic semibenzoquinone.


Chemical Structure

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Jacaranone
CAS# 60263-07-2

Theoretical Analysis

MedKoo Cat#: 596093
Name: Jacaranone
CAS#: 60263-07-2
Chemical Formula: C9H10O4
Exact Mass: 182.0579
Molecular Weight: 182.17
Elemental Analysis: C, 59.34; H, 5.53; O, 35.13

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.

Request quote for custom synthesis

Synonym: Jacaranone;

IUPAC/Chemical Name: methyl 2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate

InChi Key: WJZSKNRPRWCLLK-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H10O4/c1-13-8(11)6-9(12)4-2-7(10)3-5-9/h2-5,12H,6H2,1H3

SMILES Code: O=C(OC)CC1(O)C=CC(C=C1)=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 182.17 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: Pereira VV, Duarte LP, Silva RR, Takahashi JA. New jacaranone glucoside from Jacaranda oxyphylla leaves. Nat Prod Res. 2016 Nov;30(21):2421-8. doi: 10.1080/14786419.2016.1195378. Epub 2016 Jun 13. PubMed PMID: 27295283.

2: Sun H, Yue PY, Wang SR, Huo L, Zhao Y, Xie S, Kringelum JV, Lund O, Taboureau O, Zhou J, Wong RN, Fang WS. Synthesis and Biological Evaluations of Cytotoxic and Antiangiogenic Triterpenoids-Jacaranone Conjugates. Med Chem. 2016;12(8):775-785. PubMed PMID: 27140183.

3: Fraga BM, Díaz CE, Amador LJ, Reina M, Santana O, González-Coloma A. Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae. Phytochemistry. 2014 Dec;108:220-8. doi: 10.1016/j.phytochem.2014.09.010. Epub 2014 Oct 6. PubMed PMID: 25301666.

4: Yi XX, Chen Y, Xie WP, Xu MB, Chen YN, Gao CH, Huang RM. Four new Jacaranone analogs from the fruits of a Beibu Gulf mangrove Avicennia marina. Mar Drugs. 2014 Apr 30;12(5):2515-25. doi: 10.3390/md12052515. PubMed PMID: 24796307; PubMed Central PMCID: PMC4052303.

5: Yan XJ, Bai XY, Liu QB, Liu S, Gao PY, Li LZ, Song SJ. Two new glycosides from the fruits of Forsythia suspense. J Asian Nat Prod Res. 2014;16(4):376-82. doi: 10.1080/10286020.2014.884082. Epub 2014 Feb 10. PubMed PMID: 24506327.

6: Rana A, Bhangalia S, Singh HP. A new phenylethanoid glucoside from Jacaranda mimosifolia. Nat Prod Res. 2013;27(13):1167-73. doi: 10.1080/14786419.2012.717290. Epub 2012 Aug 29. PubMed PMID: 22928593.

7: Massaoka MH, Matsuo AL, Figueiredo CR, Farias CF, Girola N, Arruda DC, Scutti JA, Romoff P, Favero OA, Ferreira MJ, Lago JH, Travassos LR. Jacaranone induces apoptosis in melanoma cells via ROS-mediated downregulation of Akt and p38 MAPK activation and displays antitumor activity in vivo. PLoS One. 2012;7(6):e38698. doi: 10.1371/journal.pone.0038698. Epub 2012 Jun 6. PubMed PMID: 22701695; PubMed Central PMCID: PMC3368838.

8: Nuringtyas TR, Choi YH, Verpoorte R, Klinkhamer PG, Leiss KA. Differential tissue distribution of metabolites in Jacobaea vulgaris, Jacobaea aquatica and their crosses. Phytochemistry. 2012 Jun;78:89-97. doi: 10.1016/j.phytochem.2012.03.011. Epub 2012 Apr 18. PubMed PMID: 22516740.

9: Yang X, Yang L, Xiong A, Li D, Wang Z. Authentication of Senecio scandens and S. vulgaris based on the comprehensive secondary metabolic patterns gained by UPLC-DAD/ESI-MS. J Pharm Biomed Anal. 2011 Sep 10;56(2):165-72. doi: 10.1016/j.jpba.2011.05.004. Epub 2011 May 12. PubMed PMID: 21664784.

10: Morais TR, Romoff P, Fávero OA, Reimão JQ, Lourenço WC, Tempone AG, Hristov AD, Di Santi SM, Lago JH, Sartorelli P, Ferreira MJ. Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae). Parasitol Res. 2012 Jan;110(1):95-101. doi: 10.1007/s00436-011-2454-9. Epub 2011 May 26. PubMed PMID: 21614544.

11: Gao Y. [Chemical constituents from Aster sampsonii]. Zhongguo Zhong Yao Za Zhi. 2010 Sep;35(17):2289-92. Chinese. PubMed PMID: 21137340.

12: Gachet MS, Kunert O, Kaiser M, Brun R, Muñoz RA, Bauer R, Schühly W. Jacaranone-derived glucosidic esters from Jacaranda glabra and their activity against Plasmodium falciparum. J Nat Prod. 2010 Apr 23;73(4):553-6. doi: 10.1021/np900528m. PubMed PMID: 20307077.

13: Wang WS, Lu P, Duan CH, Feng JC. A new jacaranone derivative from Senecio scandens var. incisus. Nat Prod Res. 2010 Mar;24(4):370-4. doi: 10.1080/14786410903250936. PubMed PMID: 20221943.

14: Lozada-Lechuga J, Villarreal ML, Fliniaux MA, Bensaddek L, Mesnard F, Gutiérrez Mdel C, Cardoso-Taketa AT. Isolation of jacaranone, a sedative constituent extracted from the flowers of the Mexican tree Ternstroemia pringlei. J Ethnopharmacol. 2010 Feb 3;127(2):551-4. doi: 10.1016/j.jep.2009.11.020. Epub 2009 Nov 29. PubMed PMID: 19951739.

15: Mezache N, Derbré S, Akkal S, Laouer H, Séraphin D, Richomme P. Fast counter current chromatography of n-butanolic fraction from Senecio giganteus (Asteraceae). Nat Prod Commun. 2009 Oct;4(10):1357-62. PubMed PMID: 19911571.

16: Tian XY, Wang YH, Yang QY, Yu SS, Fang WS. Jacaranone analogs from Senecio scandens. J Asian Nat Prod Res. 2009;11(1):63-8. doi: 10.1080/10286020802413239. PubMed PMID: 19177240.

17: Leiss KA, Choi YH, Abdel-Farid IB, Verpoorte R, Klinkhamer PG. NMR metabolomics of thrips (Frankliniella occidentalis) resistance in Senecio hybrids. J Chem Ecol. 2009 Feb;35(2):219-29. doi: 10.1007/s10886-008-9586-0. Epub 2009 Jan 24. PubMed PMID: 19169751.

18: Gachet MS, Schühly W. Jacaranda--an ethnopharmacological and phytochemical review. J Ethnopharmacol. 2009 Jan 12;121(1):14-27. doi: 10.1016/j.jep.2008.10.015. Epub 2008 Nov 1. Review. PubMed PMID: 19010407.

19: Ma HY, Yang L, Zhang M, Wang CH, Wang ZT. A new compound from Senecio cannabifolius var integrilifolius. Yao Xue Xue Bao. 2008 Jun;43(6):626-9. PubMed PMID: 18822966.

20: Loizzo MR, Tundis R, Statti GA, Menichini F. Jacaranone: a cytotoxic constituent from Senecio ambiguus subsp. ambiguus (biv.) DC. against renal adenocarcinoma ACHN and prostate carcinoma LNCaP cells. Arch Pharm Res. 2007 Jun;30(6):701-7. PubMed PMID: 17679547.