1,3,5-Trihydroxyxanthone

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

MedKoo CAT#: 526087

CAS#: 6732-85-0

Description: 1,3,5-Trihydroxyxanthone is a highly cytotoxic natural compound against a range of bacteria and yeasts; Anti-androgenic.


Price and Availability

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1,3,5-Trihydroxyxanthone 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#: 526087
Name: 1,3,5-Trihydroxyxanthone
CAS#: 6732-85-0
Chemical Formula: C13H8O5
Exact Mass: 244.0372
Molecular Weight: 244.202
Elemental Analysis: C, 63.94; H, 3.30; O, 32.76


Synonym: 1,3,5-Trihydroxyxanthone

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

InChi Key: XESIWQIMUSNPRO-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H8O5/c14-6-4-9(16)11-10(5-6)18-13-7(12(11)17)2-1-3-8(13)15/h1-5,14-16H

SMILES Code: O=C1C2=C(OC3=C1C=CC=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: El-Awaad I, Bocola M, Beuerle T, Liu B, Beerhues L. Bifunctional CYP81AA proteins catalyse identical hydroxylations but alternative regioselective phenol couplings in plant xanthone biosynthesis. Nat Commun. 2016 May 5;7:11472. doi: 10.1038/ncomms11472. PubMed PMID: 27145837; PubMed Central PMCID: PMC4858744.

2: He K, Cao TW, Wang HL, Geng CA, Zhang XM, Chen JJ. [Chemical constituents of Swertia patens]. Zhongguo Zhong Yao Za Zhi. 2015 Oct;40(20):4012-7. Chinese. PubMed PMID: 27062819.

3: Ali M, Latif A, Zaman K, Arfan M, Maitland D, Ahmad H, Ahmad M. Anti-ulcer xanthones from the roots of Hypericum oblongifolium Wall. Fitoterapia. 2014 Jun;95:258-65. doi: 10.1016/j.fitote.2014.03.014. Epub 2014 Mar 29. PubMed PMID: 24685505.

4: Wang G, Shi G, Chen X, Chen F, Yao R, Wang Z. Loading of free radicals on the functional graphene combined with liquid chromatography-tandem mass spectrometry screening method for the detection of radical-scavenging natural antioxidants. Anal Chim Acta. 2013 Nov 13;802:103-12. doi: 10.1016/j.aca.2013.09.041. Epub 2013 Sep 30. PubMed PMID: 24176511.

5: Jantan I, Saputri FC. Benzophenones and xanthones from Garcinia cantleyana var. cantleyana and their inhibitory activities on human low-density lipoprotein oxidation and platelet aggregation. Phytochemistry. 2012 Aug;80:58-63. doi: 10.1016/j.phytochem.2012.05.003. Epub 2012 May 26. PubMed PMID: 22640928.

6: Lin CF, Chen YJ, Huang YL, Chiou WF, Chiu JH, Chen CC. A new auronol from Cudrania cochinchinensis. J Asian Nat Prod Res. 2012;14(7):704-7. doi: 10.1080/10286020.2012.682305. Epub 2012 May 15. PubMed PMID: 22582907.

7: Ali M, Arfan M, Ahmad M, Singh K, Anis I, Ahmad H, Choudhary MI, Shah MR. Anti-inflammatory xanthones from the twigs of Hypericum oblongifolium wall. Planta Med. 2011 Dec;77(18):2013-8. doi: 10.1055/s-0031-1280114. Epub 2011 Aug 25. PubMed PMID: 21870324.

8: Lannang AM, Louh GN, Biloa BM, Komguem J, Mbazoa CD, Sondengam BL, Naesens L, Pannecouque C, De Clercq E, Sayed El Ashry el H. Cytotoxicity of natural compounds isolated from the seeds of Garcinia afzelii. Planta Med. 2010 May;76(7):708-12. doi: 10.1055/s-0029-1240627. Epub 2009 Nov 20. PubMed PMID: 19937549.

9: Wang LL, Li ZL, Hua HM, Liu XQ. [Chemical constituents from barks of Garcinia tetralata]. Zhongguo Zhong Yao Za Zhi. 2008 Oct;33(20):2350-2. Chinese. PubMed PMID: 19157125.

10: 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.

11: Komguem J, Meli AL, Manfouo RN, Lontsi D, Ngounou FN, Kuete V, Kamdem HW, Tane P, Ngadjui BT, Sondengam BL, Connolly JD. Xanthones from Garcinia smeathmannii (Oliver) and their antimicrobial activity. Phytochemistry. 2005 Jul;66(14):1713-7. PubMed PMID: 15907961.

12: Hay AE, Hélesbeux JJ, Duval O, Labaïed M, Grellier P, Richomme P. Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii. Life Sci. 2004 Nov 5;75(25):3077-85. PubMed PMID: 15474559.

13: Zeng GY, Tan GS, Xu KP, Xu XP, Li FS, Tan JB, Hu GY. [Water-soluble chemical constituents of Swertia davidi Franch]. Yao Xue Xue Bao. 2004 May;39(5):351-3. Chinese. PubMed PMID: 15338877.

14: 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.

15: Zhang Z, ElSohly HN, Jacob MR, Pasco DS, Walker LA, Clark AM. Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii. Planta Med. 2002 Jan;68(1):49-54. PubMed PMID: 11842327.

16: Schmidt W, Peters S, Beerhues L. Xanthone 6-hydroxylase from cell cultures of Centaurium erythraea RAFN and Hypericum androsaemium L. Phytochemistry. 2000 Feb;53(4):427-31. PubMed PMID: 10731018.

17: Wu QL, Wang SP, Du LJ, Yang JS, Xiao PG. Xanthones from Hypericum japonicum and H. henryi. Phytochemistry. 1998 Nov;49(5):1395-402. PubMed PMID: 9842731.