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.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-10-29. Prices are subject to change without notice.

Umbelliprenin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


Synonym: Angelin, Umbelliprenin

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


Technical Data

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


References

1: 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. PubMed PMID: 30127820; PubMed Central PMCID: PMC6094438.

2: 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. PubMed PMID: 29797576.

3: Khaghanzadeh N, Samiei A, Mojtahedi Z, Ramezani M, Hosseinzadeh M, Ghaderi A. Umbelliprenin induced both anti-inflammatory and regulatory cytokines in C57/BL6 mice. Iran J Basic Med Sci. 2017 Jul;20(7):829-834. doi: 10.22038/IJBMS.2017.9021. PubMed PMID: 28852449; PubMed Central PMCID: PMC5569593.

4: Khaghanzadeh N, Nakamura K, Kuramitsu Y, Ghaderi A, Mojtahedi Z. Immune-associated proteins with potential in vivo anti-tumor activities are upregulated in lung cancer cells treated with umbelliprenin: A proteomic approach. Oncol Lett. 2016 Dec;12(6):5295-5302. doi: 10.3892/ol.2016.5352. Epub 2016 Nov 4. PubMed PMID: 28105238; PubMed Central PMCID: PMC5228441.

5: Rashidi M, Ziai SA, Moini Zanjani T, Khalilnezhad A, Jamshidi H, Amani D. Umbelliprenin is Potentially Toxic Against the HT29, CT26, MCF-7, 4T1, A172, and GL26 Cell Lines, Potentially Harmful Against Bone Marrow-Derived Stem Cells, and Non-Toxic Against Peripheral Blood Mononuclear Cells. Iran Red Crescent Med J. 2016 May 14;18(7):e35167. eCollection 2016 Jul. PubMed PMID: 27703798; PubMed Central PMCID: PMC5027671.

6: Khaghanzadeh N, Samiei A, Ramezani M, Mojtahedi Z, Hosseinzadeh M, Ghaderi A. Umbelliprenin induced production of IFN-γ and TNF-α, and reduced IL-10, IL-4, Foxp3 and TGF-β in a mouse model of lung cancer. Immunopharmacol Immunotoxicol. 2014 Feb;36(1):25-32. doi: 10.3109/08923973.2013.863912. Epub 2013 Dec 11. PubMed PMID: 24325354.

7: Khaghanzadeh N, Mojtahedi Z, Ramezani M, Erfani N, Ghaderi A. Umbelliprenin is cytotoxic against QU-DB large cell lung cancer cell line but anti-proliferative against A549 adenocarcinoma cells. Daru. 2012 Oct 30;20(1):69. doi: 10.1186/2008-2231-20-69. PubMed PMID: 23351548; PubMed Central PMCID: PMC3556042.

8: Ziai SA, Gholami O, Iranshahi M, Zamani AH, Jeddi-Tehrani M. Umbelliprenin Induces Apoptosis in CLL Cell Lines. Iran J Pharm Res. 2012 Spring;11(2):653-9. PubMed PMID: 24250490; PubMed Central PMCID: PMC3832171.

9: Iranshahi M, Sahebkar A, Takasaki M, Konoshima T, Tokuda H. Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo. Eur J Cancer Prev. 2009 Sep;18(5):412-5. doi: 10.1097/CEJ.0b013e32832c389e. PubMed PMID: 19531956.

10: Barthomeuf C, Lim S, Iranshahi M, Chollet P. Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis. Phytomedicine. 2008 Jan;15(1-2):103-11. Epub 2007 Aug 8. PubMed PMID: 17689942.