Jacareubin

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

MedKoo CAT#: 414254

CAS#: 3811-29-8

Description: Jacareubin, as known as xanthone III, is a natural product isolated from plants such as Calophyllum brasiliense Cambess. (Clusiaceae), and Mammea americana L. (Clusiaceae). Jacareubin inhibits FcεRI-induced extracellular calcium entry and production of reactive oxygen species required for anaphylactic degranulation of mast cells


Chemical Structure

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Jacareubin
CAS# 3811-29-8

Theoretical Analysis

MedKoo Cat#: 414254
Name: Jacareubin
CAS#: 3811-29-8
Chemical Formula: C18H14O6
Exact Mass: 326.079
Molecular Weight: 326.3
Elemental Analysis: C, 66.26; H, 4.32; O, 29.42

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: xanthone III; xanthoneIII; xanthone-III; Jacareubin

IUPAC/Chemical Name: 5,9,10-trihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

InChi Key: UCLUVPCGXYTYEK-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H14O6/c1-18(2)6-5-8-11(24-18)7-12-13(14(8)20)15(21)9-3-4-10(19)16(22)17(9)23-12/h3-7,19-20,22H,1-2H3

SMILES Code: CC1(C)C=CC2=C(C=C3C(C(C4=C(C(O)=C(O)C=C4)O3)=O)=C2O)O1

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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 326.3 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: Khoobchandani M, Katti KK, Karikachery AR, Thipe VC, Srisrimal D, Dhurvas Mohandoss DK, Darshakumar RD, Joshi CM, Katti KV. New Approaches in Breast Cancer Therapy Through Green Nanotechnology and Nano-Ayurvedic Medicine - Pre- Clinical and Pilot Human Clinical Investigations. Int J Nanomedicine. 2020 Jan 13;15:181-197. doi: 10.2147/IJN.S219042. PMID: 32021173; PMCID: PMC6970107.

2: Tsujimoto T, Nishihara M, Osumi Y, Hakamatsuka T, Goda Y, Uchiyama N, Ozeki Y. Structural Analysis of Polygalaxanthones, C-Glucosyl Xanthones of Polygala tenuifolia Roots. Chem Pharm Bull (Tokyo). 2019;67(11):1242-1247. doi: 10.1248/cpb.c19-00608. PMID: 31685751.

3: Li L, Liu M, Cao M, He T, Bai X. Research progress on SIRT1 and sepsis. Histol Histopathol. 2019 Nov;34(11):1205-1215. doi: 10.14670/HH-18-146. Epub 2019 Jul 8. PMID: 31282985.

4: Kózka M, Słoczyńska K, Szkaradek N, Waszkielewicz AM, Pękala E, Marona H. Effect of some newly synthesized xanthone and piperazine derivatives with cardiovascular activity on rheology of human erythrocytes in vitro. Clin Hemorheol Microcirc. 2017;67(1):1-14. doi: 10.3233/CH-16001A. PMID: 27567798.

5: Kaur P, Gupta RC, Dey A, Malik T, Pandey DK. Optimization of salicylic acid and chitosan treatment for bitter secoiridoid and xanthone glycosides production in shoot cultures of Swertia paniculata using response surface methodology and artificial neural network. BMC Plant Biol. 2020 May 19;20(1):225. doi: 10.1186/s12870-020-02410-7. PMID: 32429895; PMCID: PMC7238632.

6: Zhang KJ, Gu QL, Yang K, Ming XJ, Wang JX. Anticarcinogenic Effects of α-Mangostin: A Review. Planta Med. 2017 Feb;83(3-04):188-202. doi: 10.1055/s-0042-119651. Epub 2016 Nov 4. PMID: 27824406.

7: Ribeiro J, Veloso C, Fernandes C, Tiritan ME, Pinto MMM. Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives. Molecules. 2019 Jan 5;24(1):180. doi: 10.3390/molecules24010180. PMID: 30621303; PMCID: PMC6337274.

8: Słoczyńska K, Waszkielewicz AM, Marona H. Preliminary assessment of mutagenic and anti-mutagenic potential of some aminoalkanolic derivatives of xanthone by use of the Vibrio harveyi assay. Mutat Res Genet Toxicol Environ Mutagen. 2014 Jul 1;768:8-13. doi: 10.1016/j.mrgentox.2014.02.007. Epub 2014 Apr 24. PMID: 24769486.

9: Ikeya Y, Sugama K, Maruno M. Xanthone C-glycoside and acylated sugar from Polygala tenuifolia. Chem Pharm Bull (Tokyo). 1994 Nov;42(11):2305-8. doi: 10.1248/cpb.42.2305. PMID: 7859329.

10: Daei Farshchi Adli A, Jahanban-Esfahlan R, Seidi K, Samandari-Rad S, Zarghami N. An overview on Vadimezan (DMXAA): The vascular disrupting agent. Chem Biol Drug Des. 2018 May;91(5):996-1006. doi: 10.1111/cbdd.13166. Epub 2018 Jan 24. PMID: 29288534.



Additional Information

In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide. Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood. It can also be used as a photocatalyst.