pimpinellin
2H-furo[2,3-h]-1-benzopyran-2-one, 5,6-dimethoxy-
 
Notes:
from heracleum laciniatum; cause of phototoxicity in patient with vitiligo.
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      Product(s):
      131-12-4 Pimpinellin
       
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CAS Number: 131-12-4Picture of molecule3D/inchi
FDA UNII: D419UK1B4L
Nikkaji Web: J5.558A
XlogP3-AA: 2.30 (est)
Molecular Weight: 246.21870000
Formula: C13 H10 O5
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:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 117.00 to  119.00 °C. @ 760.00 mm Hg
Boiling Point: 441.00 to  442.00 °C. @ 760.00 mm Hg (est)
Flash Point: 429.00 °F. TCC ( 220.50 °C. ) (est)
logP (o/w): 1.477 (est)
Soluble in:
 alcohol
 water, 871.1 mg/L @ 25 °C (est)
Insoluble in:
 water
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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:
Alfa Biotechnology
For experimental / research use only.
Pimpinellin 98%
BOC Sciences
For experimental / research use only.
Pimpinellin
Coompo
For experimental / research use only.
Pimpinellin from Plants ≥96%
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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 pimpinellin usage levels up to:
 not for fragrance use.
 
Recommendation for pimpinellin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 4825
National Institute of Allergy and Infectious Diseases: Data
 5,6-dimethoxyfuro[2,3-h]chromen-2-one
Chemidplus: 0000131124
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References:
 5,6-dimethoxyfuro[2,3-h]chromen-2-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 4825
Pubchem (sid): 135024782
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C09285
HMDB (The Human Metabolome Database): Search
FooDB: FDB006436
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
EFSA Update of results on the monitoring of furan levels in food: Read Report
EFSA Previous report: Results on the monitoring of furan levels in food: Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food: Read Report
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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
 heracleum maximum root
Search Trop  Picture
 parsnip plant
Search Trop  Picture
 pimpinella sazifraga
Search Trop  Picture
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Synonyms:
5,6-dimethoxy-2H-furo(2,3-h)-1-benzopyran-2-one
5,6-dimethoxy-2H-furo[2,3-h]-1-benzopyran-2-one
5,6-dimethoxy-2H-furo[2,3-h]chromen-2-one
5,6-dimethoxyfurano-4,5,7,8-coumarin
5,6-dimethoxyfuro[2,3-h]chromen-2-one
2H-furo(2,3-h)-1-benzopyran-2-one, 5,6-dimethoxy-
2H-furo[2,3-h]-1-benzopyran-2-one, 5,6-dimethoxy-
4-hydroxy-6,7-dimethoxy-5-benzofuranacrylic acid d-lactone
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Articles:
PubMed: Simultaneous determination of 12 coumarins in bamboo leaves by HPLC.
PubMed: Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry.
PubMed: The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.
PubMed: Discovery and antitumor activities of constituents from Cyrtomium fortumei (J.) Smith rhizomes.
PubMed: Determination of cnidilin and its two metabolites in rat plasma by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry.
PubMed: Determination of cnidilin and its two metabolites in rat bile and stool after oral administration by HPLC/electrospray ionization tandem mass spectrometry.
PubMed: Separation and purification of furanocoumarins from Toddalia asiatica (L.) Lam. using microwave-assisted extraction coupled with high-speed counter-current chromatography.
PubMed: Simultaneous determination of pimpinellin, isopimpinellin and phellopterin in rat plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of Toddalia asiatica extract.
PubMed: Changes in the phenolic and lipophilic composition, in the enzyme inhibition and antiproliferative activity of Ficus carica L. cultivar Dottato fruits during maturation.
PubMed: Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry.
PubMed: Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry.
PubMed: Simultaneous and sensitive determination of xanthotoxin, psoralen, isoimpinellin and bergapten in rat plasma by liquid chromatography-electrospray ionization mass spectrometry.
PubMed: Phytophotodermatitis in Rijeka region, Croatia.
PubMed: Supercritical fluid extraction for identification and determination of volatile metabolites from Angelica dahurica by GC-MS.
PubMed: A pimpinellin monomer and dimer isolated from the roots of Esenbeckia grandiflora.
PubMed: Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica.
PubMed: The furanocoumarins in the roots of Heracleum sibiricum L.
PubMed: Inducible nitric oxide synthase inhibitors of Chinese herbs. Part 2: naturally occurring furanocoumarins.
PubMed: Rapid determination of furanocoumarins in creams and pomades using SPE and GC.
PubMed: Isolation And Structure Elucidation Of 5,7-disubstituted Simple Coumarins In The Fruits Of Heracleum Mantegazzianum.
PubMed: Identification of eight coumarins occurring with psoralen, xanthotoxin, and bergapten on leaf surfaces.
PubMed: Heracleum mantegazzianum growth phases and furocoumarin content.
PubMed: Identification of psoralen, 8-methoxypsoralen, isopimpinellin, and 5,7-dimethoxycoumarin in Pelea anisata H. Mann.
PubMed: Phototoxicity from furocoumarins (psoralens) of Heracleum laciniatum in a patient with vitiligo. Action spectrum studies on bergapten, pimpinellin, angelicin and sphondin.
PubMed: Furocoumarins of Heracleum laciniatum: isolation, phototoxicity, absorption and action spectra studies.
PubMed: Accidental induction of photocontact allergy to Heracleum laciniatum.
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