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MedKoo Cat#: 573330 | Name: Aurapten
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Description:

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

Aurapten is a coumarin with anti-inflammatory, anti-carcinogenic, anti-bacterial, neuroprotective, and hepatoprotective activities. It inhibits leukocyte activation and induces phase II enzymes during the initiation phase of carcinogenesis. Aurapten may also be useful in the treatment of Alzheimer’s disease by inhibiting β-secretase (BACE1) activity.

Chemical Structure

Aurapten
Aurapten
CAS#495-02-3

Theoretical Analysis

MedKoo Cat#: 573330

Name: Aurapten

CAS#: 495-02-3

Chemical Formula: C19H22O3

Exact Mass: 298.1569

Molecular Weight: 298.38

Elemental Analysis: C, 76.48; H, 7.43; O, 16.09

Price and Availability

Size Price Availability Quantity
50mg USD 265.00 2 Weeks
100mg USD 485.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
7-Geranyloxycoumarin, Aurapten, Auraptene
IUPAC/Chemical Name
2H-1-Benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-
InChi Key
RSDDHGSKLOSQFK-RVDMUPIBSA-N
InChi Code
1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
SMILES Code
CC(=CCC/C(=C/COc1ccc2ccc(=O)oc2c1)/C)C
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 298.38 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: Napolitano HB, Silva M, Ellena J, Rodrigues BD, Almeida AL, Vieira PC, Oliva G, Thiemann OH. Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes. Braz J Med Biol Res. 2004 Dec;37(12):1847-52. doi: 10.1590/s0100-879x2004001200010. Epub 2004 Nov 17. PMID: 15558191. 2: Yamada Y, Okamoto M, Kikuzaki H, Nakatani N. Spasmolytic activity of aurapten analogs. Biosci Biotechnol Biochem. 1997 Apr;61(4):740-2. doi: 10.1271/bbb.61.740. PMID: 9145535. 3: Takahashi Y, Inaba N, Kuwahara S, Kuki W, Yamane K, Murakami A. Rapid and convenient method for preparing aurapten-enriched product from hassaku peel oil: implications for cancer-preventive food additives. J Agric Food Chem. 2002 May 22;50(11):3193-6. doi: 10.1021/jf011628b. PMID: 12009985. 4: Fiorito S, Epifano F, Marchetti L, Genovese S. Semisynthesis of Selenoauraptene. Molecules. 2021 May 10;26(9):2798. doi: 10.3390/molecules26092798. PMID: 34068532; PMCID: PMC8126015. 5: Derosa G, Maffioli P, Sahebkar A. Auraptene and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:399-407. doi: 10.1007/978-3-319-41342-6_19. PMID: 27771936. 6: Kohno S, Murata T, Sugiura A, Ito C, Iranshahi M, Hikita K, Kaneda N. Methyl galbanate, a novel inhibitor of nitric oxide production in mouse macrophage RAW264.7 cells. J Nat Med. 2011 Apr;65(2):353-9. doi: 10.1007/s11418-010-0505-7. Epub 2011 Jan 19. PMID: 21246298. 7: Yerer MB, Dayan S, Han MI, Sharma A, Tuli HS, Sak K. Nanoformulations of Coumarins and the Hybrid Molecules of Coumarins with Potential Anticancer Effects. Anticancer Agents Med Chem. 2020;20(15):1797-1816. doi: 10.2174/1871520620666200310094646. PMID: 32156246. 8: Reisch J, Szendrei K, Minker E, Novák I. Notiz über das Vorkommen von Aurapten in Dictamnus albus [Note on the presence of aurapten in Dictamnus albus]. Planta Med. 1967 Aug;15(3):320-2. German. doi: 10.1055/s-0028-1099989. PMID: 5618643. 9: Kurdelas RR, Lima B, Tapia A, Feresin GE, Gonzalez Sierra M, Rodríguez MV, Zacchino S, Enriz RD, Freile ML. Antifungal activity of extracts and prenylated coumarins isolated from Baccharis darwinii Hook & Arn. (Asteraceae). Molecules. 2010 Jul 13;15(7):4898-907. doi: 10.3390/molecules15074898. PMID: 20657398; PMCID: PMC6257657. 10: Johann S, Mendes BG, Missau FC, de Resende MA, Pizzolatti MG. Antifungal activity of five species of Polygala. Braz J Microbiol. 2011 Jul;42(3):1065-75. doi: 10.1590/S1517-838220110003000027. Epub 2011 Sep 1. PMID: 24031724; PMCID: PMC3768791. 11: Bibak B, Shakeri F, Barreto GE, Keshavarzi Z, Sathyapalan T, Sahebkar A. A review of the pharmacological and therapeutic effects of auraptene. Biofactors. 2019 Nov;45(6):867-879. doi: 10.1002/biof.1550. Epub 2019 Aug 19. PMID: 31424600. 12: Nugroho AE, Agistia DD, Tegar M, Purnomo H. Interaction of active compounds from Aegle marmelos CORREA with histamine-1 receptor. Bioinformation. 2013 Apr 30;9(8):383-7. doi: 10.6026/97320630009383. PMID: 23750086; PMCID: PMC3670119. 13: Kakiuchi N, Senaratne LR, Huang SL, Yang XW, Hattori M, Pilapitiya U, Namba T. Effects of constituents of Beli (Aegle marmelos) on spontaneous beating and calcium-paradox of myocardial cells. Planta Med. 1991 Feb;57(1):43-6. doi: 10.1055/s-2006-960014. PMID: 2062957. 14: Shakeri A, Iranshahy M, Iranshahi M. Biological properties and molecular targets of umbelliprenin--a mini-review. J Asian Nat Prod Res. 2014;16(8):884-9. doi: 10.1080/10286020.2014.917630. Epub 2014 May 22. PMID: 24852499. 15: Rehuman NA, Mathew B, Jat RK, Nicolotti O, Kim H. A Comprehensive Review of Monoamine Oxidase-A Inhibitors in their Syntheses and Potencies. Comb Chem High Throughput Screen. 2020;23(9):898-914. doi: 10.2174/1386207323666200428091306. PMID: 32342809. 16: Chen IS, Lin YC, Tsai IL, Teng CM, Ko FN, Ishikawa T, Ishii H. Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium. Phytochemistry. 1995 Jul;39(5):1091-7. doi: 10.1016/0031-9422(95)00054-b. PMID: 7662272. 17: Furukawa Y. [Search for Neuroprotective Compounds -From 4-Methycatechol to Citrus Compounds]. Yakugaku Zasshi. 2021;141(1):67-79. Japanese. doi: 10.1248/yakushi.20-00164. PMID: 33390450. 18: Genovese S, Epifano F. Auraptene: a natural biologically active compound with multiple targets. Curr Drug Targets. 2011 Mar 1;12(3):381-6. doi: 10.2174/138945011794815248. PMID: 20955144. 19: Kitano M, Wanibuchi H, Kikuzaki H, Nakatani N, Imaoka S, Funae Y, Hayashi S, Fukushima S. Chemopreventive effects of coumaperine from pepper on the initiation stage of chemical hepatocarcinogenesis in the rat. Jpn J Cancer Res. 2000 Jul;91(7):674-80. doi: 10.1111/j.1349-7006.2000.tb00998.x. PMID: 10920273; PMCID: PMC5926419. 20: Genovese S, Fiorito S, Epifano F, Taddeo VA. A Novel Class of Emerging Anticancer Compounds: Oxyprenylated Secondary Metabolites from Plants and Fungi. Curr Med Chem. 2015;22(30):3426-33. doi: 10.2174/0929867322666150716114758. PMID: 26180000.