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MedKoo Cat#: 573158 | Name: Umbelliprenin

Description:

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

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

Chemical Structure

Umbelliprenin
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: 366.50

Elemental Analysis: C, 78.65; H, 8.25; O, 13.10

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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

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
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Assessment of the Antitumor Potential of Umbelliprenin, a Naturally Occurring Sesquiterpene Coumarin. Biomedicines. 2020 May 18;8(5):126. doi: 10.3390/biomedicines8050126. PMID: 32443431; PMCID: PMC7277383. 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. 6: 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. 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. 16: Iranshahi M, Rezaee R, Najaf Najafi M, Haghbin A, Kasaian J. Cytotoxic activity of the genus Ferula (Apiaceae) and its bioactive constituents. Avicenna J Phytomed. 2018 Jul-Aug;8(4):296-312. PMID: 30377589; PMCID: PMC6204145. 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.