umbelliprenin
2H-1-benzopyran-2-one, 7-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]oxy]-
Identification
| Name | umbelliprenin |
| IUPAC | 7-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]chromen-2-one |
| CAS Number | 30413-87-7 |
| FDA UNII | MSD8N8A1LQ |
| Molecular Formula | C24 H30 O3 |
| Molecular Weight | 366.50070000 |
| Nikkaji Number | J3.017.857B |
| XlogP3 | 7.10 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 512.60 °C. @ 760.00 mm Hg (est) |
| Flash Point | 432.00 °F. TCC ( 222.30 °C. ) (est) |
| logP (o/w) | 7.730 (est) |
| Soluble in | water, 0.0007348 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for umbelliprenin usage levels up to | not for fragrance use. |
| Recommendation for umbelliprenin flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
angelin
2H-1-
benzopyran-2-one, 7-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]oxy]-
coumarin, 7-((3,7,22-trimethyl-2,6,10-dodecatrienyl)oxy)-
7-[(2E,6E)-3,7,11-
trimethyldodeca-2,6,10-trienoxy]chromen-2-one
PubMed:
Mcl-1 Is Up Regulated by Prenylated Coumarin, Umbelliprenin in Jurkat Cells.
PubMed:
Biological properties and molecular targets of umbelliprenin--a mini-review.
PubMed:
Potent and selective inhibitors of class A β-lactamase: 7-prenyloxy coumarins.
PubMed:
Relaxant effects of asafoetida extract and its constituent umbelliprenin on guinea-pig tracheal smooth muscle.
PubMed:
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.
PubMed:
Umbelliprenin from Ferula szowitsiana Activates both Intrinsic and Extrinsic Pathways of Apoptosis in Jurkat T-CLL cell line.
PubMed:
Cytotoxic activities of phytochemicals from Ferula species.
PubMed:
Umbelliprenin is cytotoxic against QU-DB large cell lung cancer cell line but anti-proliferative against A549 adenocarcinoma cells.
PubMed:
Umbelliprenin Induces Apoptosis in CLL Cell Lines.
PubMed:
Methyl galbanate, a novel inhibitor of nitric oxide production in mouse macrophage RAW264.7 cells.
PubMed:
Identification of non-alkaloid acetylcholinesterase inhibitors from Ferulago campestris (Besser) Grecescu (Apiaceae).
PubMed:
New sesquiterpene coumarins from the roots of Ferula flabelliloba.
PubMed:
Galbanic acid, a cytotoxic sesquiterpene from the gum resin of Ferula asafoetida, blocks protein farnesyltransferase.
PubMed:
Two new sesquiterpene derivatives from the Tunisian endemic Ferula tunetana Pom.
PubMed:
Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo.
PubMed:
Evaluation of antigenotoxicity effects of umbelliprenin on human peripheral lymphocytes exposed to oxidative stress.
PubMed:
Cancer chemopreventive activity of terpenoid coumarins from Ferula species.
PubMed:
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.
PubMed:
A novel cytotoxic lignan from Seseli annuum L.
PubMed:
Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes.
PubMed:
Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa.
PubMed:
Two matrix metalloproteinases inhibitors from Ferula persica var. persica.
PubMed:
Bleaching of Serratia marcescens by some coumarins: a spectrophotometric study.
PubMed:
Umbelliprenin from Ferula persica roots inhibits the red pigment production in Serratia marcescens.
PubMed:
Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors.
PubMed:
Constituents of Peucedanum zenkeri seeds and their antimicrobial effects.
PubMed:
Natural coumarins. XII. Umbelliprenin, a constituent of ammi majus L. fruits.