umbelliprenin
2H-1-benzopyran-2-one, 7-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]oxy]-
 
Notes:
Isol. from Angelica archangelica (angelica)
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CAS Number: 30413-87-7Picture of molecule3D/inchi
FDA UNII: MSD8N8A1LQ
Nikkaji Web: J3.017.857B
XlogP3: 7.10 (est)
Molecular Weight: 366.50070000
Formula: C24 H30 O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 1781413
National Institute of Allergy and Infectious Diseases: Data
 7-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]chromen-2-one
Chemidplus: 0030413877
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References:
 7-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]chromen-2-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 1781413
Pubchem (sid): 135159159
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB30597
FooDB: FDB002491
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 angelica
Search Trop  Picture
 coriander fruit
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 coriander seed
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 dill seed
Search Trop  Picture
 dill seed oil
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 lemon shoot
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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
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Articles:
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.
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