apiin
7-O-(b-D-apiofuranosyl-1,2-b-D-glucosyl)-5,7,4'-trihydroxyflavone
 
Notes:
Constit. of parsley (Petroselinum crispum) and of the flowers of Anthemis nobilis (Roman chamomile). First isol. in 1843 Apiin is a chemical compound isolated from parsley and celery.
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      Product(s):
      26544-34-3 Apiin
       
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CAS Number: 26544-34-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 247-780-0
FDA UNII: 6QU3EZE37U
Nikkaji Web: J41.409C
MDL: MFCD00016941
XlogP3-AA: -0.40 (est)
Molecular Weight: 564.49796000
Formula: C26 H28 O14
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
Boiling Point: 942.20 °C. @ 760.00 mm Hg (est)
Flash Point: 602.00 °F. TCC ( 316.70 °C. ) (est)
logP (o/w): 0.720 (est)
Soluble in:
 water, 3889 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:
Alfa Biotechnology
For experimental / research use only.
Apiin 98%
BOC Sciences
For experimental / research use only.
Apiin
Carbosynth
For experimental / research use only.
Apiin
Coompo
For experimental / research use only.
Apiin from Plants ≥98%
Santa Cruz Biotechnology
For experimental / research use only.
Apiin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Apiin ≥97.0% (HPLC)
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Safety Information:
Preferred SDS: View
 
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 apiin usage levels up to:
 not for fragrance use.
 
Recommendation for apiin 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 : 5280746
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
Chemidplus: 0026544343
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References:
 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5280746
Pubchem (sid): 135116737
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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): C04858
HMDB (The Human Metabolome Database): HMDB30843
FooDB: FDB002801
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
 cayenne fruit
Search Trop  Picture
 celery plant
Search Trop  Picture
 celery seed
Search Trop  Picture
 chamomile garden chamomile plant
Search Trop  Picture
 chamomile roman chamomile flower
Search Trop  Picture
 chamomile sweet false chamomile flower
Search Trop  Picture
 chervil plant
Search Trop  Picture
 cumin seed
Search Trop  Picture
 parsley leaf
Search Trop  Picture
 parsley plant
Search Trop  Picture
 parsley seed
Search Trop  Picture
 parsley shoot
Search Trop  Picture
 parsley tissue culture
Search Trop  Picture
 pepper bell pepper fruit
Search Trop  Picture
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Synonyms:
 apigenin 7-O-[b-D-apiosyl-(1->2)-β-D-glucoside]
7-((2-O-D-apio-b-D-furanosyl-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
7-[(2-O-D-apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one
7-((2-O-dextro-apio-beta-dextro-furanosyl-beta-dextro-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
7-O-(b-D-apiofuranosyl-1,2-b-D-glucosyl)-5,7,4'-trihydroxyflavone
7-((2-O-b-D-apiofuranosyl-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone
 apioside
4H-1-benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-7-[[2-O-[(2S,3R,4R)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)-2-furanyl]-β-D-glucopyranosyl]oxy]-
7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydro-2-furanyl]-β-D-glucopyranoside
5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-b-D-glucopyranoside
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Articles:
PubMed: An extract of Apium graveolens var. dulce leaves: structure of the major constituent, apiin, and its anti-inflammatory properties.
PubMed: Biological synthesis of silver and gold nanoparticles using apiin as reducing agent.
PubMed: In vitro and in vivo antioxidant activities of a flavonoid isolated from celery (Apium graveolens L. var. dulce).
PubMed: Bioavailability of apigenin from apiin-rich parsley in humans.
PubMed: Compounds from Sedum caeruleum with antioxidant, anticholinesterase, and antibacterial activities.
PubMed: [Some physiological properties of apiin].
PubMed: Effects of blanching on polyphenol stability of innovative paste-like parsley (Petroselinum crispum (Mill.) Nym ex A. W. Hill) and marjoram (Origanum majorana L.) products.
PubMed: Identification of a new angiotensin-converting enzyme (ACE) inhibitor from Thai edible plants.
PubMed: Parsley: a review of ethnopharmacology, phytochemistry and biological activities.
PubMed: Phenolic chemical composition of Petroselinum crispum extract and its effect on haemostasis.
PubMed: Evaluation of analytical markers characterising different drying methods of parsley leaves (Petroselinum crispum L.).
PubMed: [Studies on the chemical constituents of the aerial parts of Seseli mairei].
PubMed: Medicinal foodstuffs. XVIII. Phytoestrogens from the aerial part of Petroselinum crispum MIll. (Parsley) and structures of 6"-acetylapiin and a new monoterpene glycoside, petroside.
PubMed: The jasmonate precursor, 12-oxo-phytodienoic acid, induces phytoalexin synthesis in Petroselinum crispum cell cultures.
PubMed: In vitro antioxidant activity of Anthriscus cerefolium L. (Hoffm.) extracts.
PubMed: Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structure-activity relationships.
PubMed: Protective effects of some flavonoids on the renal cellular membrane.
PubMed: Protection by naringin and some other flavonoids of hepatocytic autophagy and endocytosis against inhibition by okadaic acid.
PubMed: Fast atom bombardment and tandem mass spectrometry for structure determination of steroid and flavonoid glycosides.
PubMed: Synthesis, characterization and properties of uridine 5'-( -D-apio-D-furanosyl pyrophosphate).
PubMed: Transfer of apiose from UDP-apiose to 7-O-(beta-D-glucosyl)-apigenin and 7-O-(beta-D-glucosyl)-chrysoeriol with an enzyme preparation from parsley.
PubMed: Inositol Metabolism in Plants. IV. Biosynthesis of Apiose in Lemna and Petroselinum.
PubMed: Anti-influenza virus activities of flavonoids from the medicinal plant Elsholtzia rugulosa.
PubMed: Antioxidant and immunomodulatory constituents of henna leaves.
PubMed: [Investigation of the in vitro antioxidant effect of Petroselinum crispum (Mill.) Nym. ex A. W. Hill].
PubMed: [Screening of phagocyte activators in plants; enhancement of TNF production by flavonoids].
PubMed: Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship.
PubMed: The actions of some vasoactive polypeptides and their antagonists on the anococcygeus muscle.
PubMed: Metabolism of apigenin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro.
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