MedKoo Cat#: 461540 | Name: Rubropunctatin

Description:

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

Rubropunctatin is a monascus pigment that exhibits very strong cancer cell proliferation inhibitory effects.

Chemical Structure

Rubropunctatin
Rubropunctatin
CAS#514-67-0

Theoretical Analysis

MedKoo Cat#: 461540

Name: Rubropunctatin

CAS#: 514-67-0

Chemical Formula: C21H22O5

Exact Mass: 354.1467

Molecular Weight: 354.40

Elemental Analysis: C, 71.17; H, 6.26; O, 22.57

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rubropunctatin; Rubropunctamine;
IUPAC/Chemical Name
2H-Furo[3,2-g][2]benzopyran-2,9(9aH)-dione, 9a-methyl-3-(1-oxohexyl)-6-(1-propenyl)-, [R-(E)]-
InChi Key
SULYDLFVUNXAMP-WKOQKXSESA-N
InChi Code
InChI=1S/C21H22O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10-12H,4,6-7,9H2,1-3H3/b8-5+/t21-/m1/s1
SMILES Code
O=C(O1)C(C(CCCCC)=O)=C2[C@]1(C)C(C3=COC(/C=C/C)=CC3=C2)=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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 354.40 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
1: Zheng Y, Zhang Y, Chen D, Chen H, Lin L, Zheng C, Guo Y. Monascus Pigment Rubropunctatin: A Potential Dual Agent for Cancer Chemotherapy and Phototherapy. J Agric Food Chem. 2016 Mar 30;64(12):2541-8. doi: 10.1021/acs.jafc.5b05343. Epub 2016 Mar 16. PubMed PMID: 26953890. 2: Zheng Y, Xin Y, Shi X, Guo Y. Anti-cancer effect of rubropunctatin against human gastric carcinoma cells BGC-823. Appl Microbiol Biotechnol. 2010 Nov;88(5):1169-77. doi: 10.1007/s00253-010-2834-6. Epub 2010 Aug 21. PubMed PMID: 20730532. 3: Zheng Y, Xin Y, Shi X, Guo Y. Cytotoxicity of Monascus pigments and their derivatives to human cancer cells. J Agric Food Chem. 2010 Sep 8;58(17):9523-8. doi: 10.1021/jf102128t. PubMed PMID: 20707312. 4: Chen D, Xue C, Chen M, Wu S, Li Z, Wang C. Effects of blue light on pigment biosynthesis of Monascus. J Microbiol. 2016 Apr;54(4):305-10. doi: 10.1007/s12275-016-6011-1. Epub 2016 Apr 1. PubMed PMID: 27033206. 5: Tam EW, Tsang CC, Lau SK, Woo PC. Polyketides, toxins and pigments in Penicillium marneffei. Toxins (Basel). 2015 Oct 30;7(11):4421-36. doi: 10.3390/toxins7114421. Review. PubMed PMID: 26529013; PubMed Central PMCID: PMC4663511. 6: Mapari SA, Hansen ME, Meyer AS, Thrane U. Computerized screening for novel producers of Monascus-like food pigments in Penicillium species. J Agric Food Chem. 2008 Nov 12;56(21):9981-9. doi: 10.1021/jf801817q. Epub 2008 Oct 9. PubMed PMID: 18841978. 7: Woo PC, Lam CW, Tam EW, Lee KC, Yung KK, Leung CK, Sze KH, Lau SK, Yuen KY. The biosynthetic pathway for a thousand-year-old natural food colorant and citrinin in Penicillium marneffei. Sci Rep. 2014 Oct 22;4:6728. doi: 10.1038/srep06728. PubMed PMID: 25335861; PubMed Central PMCID: PMC4205486. 8: Dhale MA, Javagal M, Puttananjaiah MH. Protective and antioxidative effect of rubropunctatin against oxidative protein damage induced by metal catalyzed reaction. Int J Biol Macromol. 2018 Sep;116:409-416. doi: 10.1016/j.ijbiomac.2018.04.170. Epub 2018 May 3. PubMed PMID: 29730002. 9: Loret MO, Morel S. Isolation and structural characterization of two new metabolites from monascus. J Agric Food Chem. 2010 Feb 10;58(3):1800-3. doi: 10.1021/jf903231p. PubMed PMID: 20030327. 10: Hsu YW, Hsu LC, Liang YH, Kuo YH, Pan TM. New bioactive orange pigments with yellow fluorescence from Monascus-fermented dioscorea. J Agric Food Chem. 2011 May 11;59(9):4512-8. doi: 10.1021/jf1045987. Epub 2011 Apr 20. PubMed PMID: 21506577. 11: Patakova P. Monascus secondary metabolites: production and biological activity. J Ind Microbiol Biotechnol. 2013 Feb;40(2):169-81. doi: 10.1007/s10295-012-1216-8. Epub 2012 Nov 20. Review. PubMed PMID: 23179468. 12: Yilmaz N, Houbraken J, Hoekstra ES, Frisvad JC, Visagie CM, Samson RA. Delimitation and characterisation of Talaromyces purpurogenus and related species. Persoonia. 2012 Dec;29:39-54. doi: 10.3767/003158512X659500. Epub 2012 Nov 12. PubMed PMID: 23606764; PubMed Central PMCID: PMC3589794. 13: Lopes FC, Tichota DM, Pereira JQ, Segalin J, Rios Ade O, Brandelli A. Pigment production by filamentous fungi on agro-industrial byproducts: an eco-friendly alternative. Appl Biochem Biotechnol. 2013 Oct;171(3):616-25. doi: 10.1007/s12010-013-0392-y. Epub 2013 Jul 20. PubMed PMID: 23873642. 14: Hsu LC, Liang YH, Hsu YW, Kuo YH, Pan TM. Anti-inflammatory properties of yellow and orange pigments from Monascus purpureus NTU 568. J Agric Food Chem. 2013 Mar 20;61(11):2796-802. doi: 10.1021/jf305521v. Epub 2013 Mar 8. PubMed PMID: 23458314. 15: Xu B, Wang Q, Sung C. Telomerase Inhibitory Effects of Red Pigment Rubropunctatin and Statin Monacolin L Isolated from Red Yeast Rice. Genes (Basel). 2017 Apr 26;8(5). pii: E129. doi: 10.3390/genes8050129. PubMed PMID: 28445391; PubMed Central PMCID: PMC5448003. 16: Carels M, Shepherd D. The effect of different nitrogen sources on pigment production and sporulation of Monascus species in submerged, shaken culture. Can J Microbiol. 1977 Oct;23(10):1360-72. PubMed PMID: 21736. 17: Martínková L, Patáková-Jůzlová P, Krent V, Kucerová Z, Havlícek V, Olsovský P, Hovorka O, Ríhová B, Veselý D, Veselá D, Ulrichová J, Prikrylová V. Biological activities of oligoketide pigments of Monascus purpureus. Food Addit Contam. 1999 Jan;16(1):15-24. PubMed PMID: 11565571. 18: Lau SKP, Tsang CC, Woo PCY. Talaromyces marneffei Genomic, Transcriptomic, Proteomic and Metabolomic Studies Reveal Mechanisms for Environmental Adaptations and Virulence. Toxins (Basel). 2017 Jun 13;9(6). pii: E192. doi: 10.3390/toxins9060192. Review. PubMed PMID: 28608842; PubMed Central PMCID: PMC5488042. 19: Akihisa T, Tokuda H, Yasukawa K, Ukiya M, Kiyota A, Sakamoto N, Suzuki T, Tanabe N, Nishino H. Azaphilones, furanoisophthalides, and amino acids from the extracts of Monascus pilosus-fermented rice (red-mold rice) and their chemopreventive effects. J Agric Food Chem. 2005 Feb 9;53(3):562-5. PubMed PMID: 15686402. 20: Vendruscolo F, Schmidell W, de Oliveira D, Ninow JL. Kinetic of orange pigment production from Monascus ruber on submerged fermentation. Bioprocess Biosyst Eng. 2017 Jan;40(1):115-121. doi: 10.1007/s00449-016-1679-5. Epub 2016 Sep 29. PubMed PMID: 27687221.