1,3,5,6-Tetrahydroxyxanthone

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

MedKoo CAT#: 525697

CAS#: 5084-31-1

Description: 1,3,5,6-Tetrahydroxyxanthone is an anti-Mycobacterium tuberculosis agent.


Price and Availability

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1,3,5,6-Tetrahydroxyxanthone is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525697
Name: 1,3,5,6-Tetrahydroxyxanthone
CAS#: 5084-31-1
Chemical Formula: C13H8O6
Exact Mass: 260.0321
Molecular Weight: 260.201
Elemental Analysis: C, 60.01; H, 3.10; O, 36.89


Synonym: 1,3,5,6-Tetrahydroxyxanthone

IUPAC/Chemical Name: 1,3,5,6-tetrahydroxy-9H-xanthen-9-one

InChi Key: CCEBJWKUMKKCDF-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H8O6/c14-5-3-8(16)10-9(4-5)19-13-6(11(10)17)1-2-7(15)12(13)18/h1-4,14-16,18H

SMILES Code: O=C1C2=C(OC3=C1C=CC(O)=C3O)C=C(O)C=C2O


Technical Data

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).

Harmonized System Code:
293490


References

1: Zubrická D, Mišianiková A, Henzelyová J, Valletta A, De Angelis G, D'Auria FD, Simonetti G, Pasqua G, Čellárová E. Xanthones from roots, hairy roots and cell suspension cultures of selected Hypericum species and their antifungal activity against Candida albicans. Plant Cell Rep. 2015 Nov;34(11):1953-62. doi: 10.1007/s00299-015-1842-5. Epub 2015 Jul 21. PubMed PMID: 26194328.

2: Stark TD, Salger M, Frank O, Balemba OB, Wakamatsu J, Hofmann T. Antioxidative compounds from Garcinia buchananii stem bark. J Nat Prod. 2015 Feb 27;78(2):234-40. doi: 10.1021/np5007873. Epub 2015 Jan 27. PubMed PMID: 25625705.

3: Chen L, Zhou Q, Li B, Liu SJ, Dong JX. A new flavonoid from Cudrania cochinchinensis. Nat Prod Res. 2015;29(13):1217-21. doi: 10.1080/14786419.2014.997234. Epub 2015 Jan 9. PubMed PMID: 25571958.

4: Blanco-Ayala T, Lugo-Huitrón R, Serrano-López EM, Reyes-Chilpa R, Rangel-López E, Pineda B, Medina-Campos ON, Sánchez-Chapul L, Pinzón E, Cristina TS, Silva-Adaya D, Pedraza-Chaverrí J, Ríos C, de la Cruz VP, Torres-Ramos M. Antioxidant properties of xanthones from Calophyllum brasiliense: prevention of oxidative damage induced by FeSO₄. BMC Complement Altern Med. 2013 Oct 11;13:262. doi: 10.1186/1472-6882-13-262. PubMed PMID: 24119308; PubMed Central PMCID: PMC3852108.

5: Araújo MG, Hilário F, Nogueira LG, Vilegas W, Santos LC, Bauab TM. Chemical constituents of the methanolic extract of leaves of Leiothrix spiralis Ruhland and their antimicrobial activity. Molecules. 2011 Dec 16;16(12):10479-90. doi: 10.3390/molecules161210479. PubMed PMID: 22179427.

6: An RB, Jeong GS, Beom JS, Sohn DH, Kim YC. Chromone glycosides and hepatoprotective constituents of Hypericum erectum. Arch Pharm Res. 2009 Oct;32(10):1393-7. doi: 10.1007/s12272-009-2008-1. Epub 2009 Nov 8. PubMed PMID: 19898802.

7: Louh GN, Lannang AM, Mbazoa CD, Tangmouo JG, Komguem J, Castilho P, Ngninzeko FN, Qamar N, Lontsi D, Choudhary MI, Sondengam BL. Polyanxanthone A, B and C, three xanthones from the wood trunk of Garcinia polyantha Oliv. Phytochemistry. 2008 Feb;69(4):1013-7. Epub 2007 Nov 26. PubMed PMID: 18022654.

8: Wang YH, Feng ZM, Jiang JS, Zhang PC. [Studies on chemical constituents from roots of Cudrania cochinchinensis]. Zhongguo Zhong Yao Za Zhi. 2007 Mar;32(5):406-9. Chinese. PubMed PMID: 17511146.

9: Nguyen LH, Venkatraman G, Sim KY, Harrison LJ. Xanthones and benzophenones from Garcinia griffithii and Garcinia mangostana. Phytochemistry. 2005 Jul;66(14):1718-23. PubMed PMID: 16173114.

10: Ferrari F, Pasqua G, Monacelli B, Cimino P, Botta B. Xanthones from calli of Hypericum perforatum subsp. perforatum. Nat Prod Res. 2005 Feb;19(2):171-6. PubMed PMID: 15715262.

11: Jiang DJ, Hu GY, Jiang JL, Xiang HL, Deng HW, Li YJ. Relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors. Bioorg Med Chem. 2003 Nov 17;11(23):5171-7. PubMed PMID: 14604680.

12: Jantan I, Pisar MM, Idris MS, Taher M, Ali RM. In vitro inhibitory effect of rubraxanthone isolated from Garcinia parvifolia on platelet-activating factor receptor binding. Planta Med. 2002 Dec;68(12):1133-4. PubMed PMID: 12494345.

13: Santos LC, Piacente S, De Riccardis F, Eletto AM, Pizza C, Vilegas W. Xanthones and flavonoids from Leiothrix curvifolia and Leiothrix flavescens. Phytochemistry. 2001 Apr;56(8):853-6. PubMed PMID: 11324917.

14: Lin CN, Liou SS, Ko FN, Teng CM. Gamma-pyrone compounds. II: Synthesis and antiplatelet effects of tetraoxygenated xanthones. J Pharm Sci. 1992 Nov;81(11):1109-12. PubMed PMID: 1447715.

15: Chen CH, Lin JY, Lin CN, Hsu SY. Inhibition of angiotensin-I-converting enzyme by tetrahydroxyxanthones isolated from Tripterospermum lanceolatum. J Nat Prod. 1992 May;55(5):691-5. PubMed PMID: 1517742.