Umbelliprenin

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

MedKoo CAT#: 573158

CAS#: 30413-87-7

Description: Umbelliprenin, also known as Angelin, is a prenyloxy-coumarin which may have anti-inflammatory, anti-tumor, antioxidant, and antigenotoxic activities.

Chemical Structure

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Umbelliprenin
CAS# 30413-87-7
Instruction

Theoretical Analysis

MedKoo Cat#: 573158
Name: Umbelliprenin
CAS#: 30413-87-7
Chemical Formula: C24H30O3
Exact Mass: 366.22
Molecular Weight: 366.500
Elemental Analysis: C, 78.65; H, 8.25; O, 13.10

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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Related CAS #: 30413-87-7   532-16-1  

Synonym: Angelin; Umbelliprenin; 7-Farnesyloxycoumarin; 7 Farnesyloxycoumarin;

IUPAC/Chemical Name: 7-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)-2H-chromen-2-one

InChi Key: GNMUGVNEWCZUAA-WOWYBKFKSA-N

InChi Code: 1S/C24H30O3/c1-18(2)7-5-8-19(3)9-6-10-20(4)15-16-26-22-13-11-21-12-14-24(25)27-23(21)17-22/h7,9,11-15,17H,5-6,8,10,16H2,1-4H3/b19-9+,20-15+

SMILES Code: c1(ccc2c(o1)cc(cc2)OC\C=C(\CC\C=C(\CC\C=C(\C)C)C)C)=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 366.50 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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3: Shahraki J, Rezaee R, Mohammadzehi Kenar S, Setoodeh Nezhad S, Bagheri G, Jahantigh H, Tsarouhas K, Hashemzaei M. Umbelliprenin relieves paclitaxel- induced neuropathy. J Pharm Pharmacol. 2020 Dec;72(12):1822-1829. doi: 10.1111/jphp.13365. Epub 2020 Sep 15. PMID: 32930406.

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5: Gkionis L, Kavetsou E, Kalospyros A, Manousakis D, Garzon Sanz M, Butterworth S, Detsi A, Tirella A. Investigation of the cytotoxicity of bioinspired coumarin analogues towards human breast cancer cells. Mol Divers. 2020 Apr 23. doi: 10.1007/s11030-020-10082-6. Epub ahead of print. PMID: 32328962.

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7: Fiorito S, Genovese S, Palumbo L, Scotti L, Ciulla M, di Profio P, Epifano F. Umbelliprenin as a novel component of the phytochemical pool from Artemisia spp. J Pharm Biomed Anal. 2020 May 30;184:113205. doi: 10.1016/j.jpba.2020.113205. Epub 2020 Feb 24. PMID: 32113116.

8: Fois B, Distinto S, Meleddu R, Deplano S, Maccioni E, Floris C, Rosa A, Nieddu M, Caboni P, Sissi C, Angeli A, Supuran CT, Cottiglia F. Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation. J Enzyme Inhib Med Chem. 2020 Dec;35(1):539-548. doi: 10.1080/14756366.2020.1713114. PMID: 31948300; PMCID: PMC7006766.

9: Ziai SA, Gholami O. Umbelliprenin, a bioactive constituent from the genus Ferula has cytotoxic and apoptotic activity in a dose- and time-dependent manner. Avicenna J Phytomed. 2020 Jan-Feb;10(1):1-2. PMID: 31921602; PMCID: PMC6941684.

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11: Zhang L, Sun X, Si J, Li G, Cao L. Umbelliprenin isolated from Ferula sinkiangensis inhibits tumor growth and migration through the disturbance of Wnt signaling pathway in gastric cancer. PLoS One. 2019 Jul 1;14(7):e0207169. doi: 10.1371/journal.pone.0207169. PMID: 31260453; PMCID: PMC6602182.

12: Fiorito S, Ianni F, Preziuso F, Epifano F, Scotti L, Bucciarelli T, Genovese S. UHPLC-UV/Vis Quantitative Analysis of Hydroxylated and O-prenylated Coumarins in Pomegranate Seed Extracts. Molecules. 2019 May 22;24(10):1963. doi: 10.3390/molecules24101963. PMID: 31121819; PMCID: PMC6572463.

13: Soltani S, Amin G, Salehi-Sourmaghi MH, Iranshahi M. Histone deacetylase inhibitory and cytotoxic activities of the constituents from the roots of three species of Ferula. Iran J Basic Med Sci. 2019 Jan;22(1):93-98. doi: 10.22038/IJBMS.2018.34338.8151. PMID: 30944714; PMCID: PMC6437461.

14: Taddeo VA, Epifano F, Preziuso F, Fiorito S, Caron N, Rives A, de Medina P, Poirot M, Silvente-Poirot S, Genovese S. HPLC Analysis and Skin Whitening Effects of Umbelliprenin-containing Extracts of Anethum Graveolens, Pimpinella Anisum, and Ferulago Campestris. Molecules. 2019 Jan 30;24(3):501. doi: 10.3390/molecules24030501. PMID: 30704124; PMCID: PMC6384930.

15: Fiorito S, Preziuso F, Epifano F, Scotti L, Bucciarelli T, Taddeo VA, Genovese S. Novel biologically active principles from spinach, goji and quinoa. Food Chem. 2019 Mar 15;276:262-265. doi: 10.1016/j.foodchem.2018.10.018. Epub 2018 Oct 5. PMID: 30409593.

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17: Naderi Alizadeh M, Rashidi M, Muhammadnejad A, Moeini Zanjani T, Ziai SA. Antitumor Effects of Umbelliprenin in a Mouse Model of Colorectal Cancer. Iran J Pharm Res. 2018 Summer;17(3):976-985. PMID: 30127820; PMCID: PMC6094438.

18: Saboormaleki S, Sadeghian H, Bahrami AR, Orafaie A, Matin MM. 7-Farnesyloxycoumarin Exerts Anti-cancer Effects on a Prostate Cancer Cell Line by 15-LOX-1 Inhibition. Arch Iran Med. 2018 Jun 1;21(6):251-259. PMID: 29940744.

19: Rashidi M, Khalilnezhad A, Amani D, Jamshidi H, Muhammadnejad A, Bazi A, Ziai SA. Umbelliprenin shows antitumor, antiangiogenesis, antimetastatic, anti- inflammatory, and immunostimulatory activities in 4T1 tumor-bearing Balb/c mice. J Cell Physiol. 2018 Nov;233(11):8908-8918. doi: 10.1002/jcp.26814. Epub 2018 May 24. PMID: 29797576.

20: Fiorito S, Epifano F, Preziuso F, Cacciatore I, di Stefano A, Taddeo VA, de Medina P, Genovese S. Natural oxyprenylated coumarins are modulators of melanogenesis. Eur J Med Chem. 2018 May 25;152:274-282. doi: 10.1016/j.ejmech.2018.04.051. Epub 2018 Apr 27. PMID: 29730190.