Umbelliprenin
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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

Theoretical Analysis

MedKoo Cat#: 573158
Name: Umbelliprenin
CAS#: 30413-87-7
Chemical Formula: C24H30O3
Exact Mass: 366.2195
Molecular Weight: 366.5
Elemental Analysis: C, 78.65; H, 8.25; O, 13.10

Price and Availability

Size Price Availability Quantity
1.0mg USD 210.0 2 Weeks
5.0mg USD 370.0 2 Weeks
10.0mg USD 590.0 2 Weeks
25.0mg USD 960.0 2 Weeks
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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

Preparing Stock Solutions

The following data is based on the product molecular weight 366.5 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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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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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.

10: Farhadi F, Asili J, Iranshahy M, Iranshahi M. NMR-based metabolomic study of asafoetida. Fitoterapia. 2019 Nov;139:104361. doi: 10.1016/j.fitote.2019.104361. Epub 2019 Oct 17. PMID: 31629871.

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.