EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

amarogentin
2-(4aS-(4aalpha,5beta,6alpha))-3,3',5-trihydroxy-(1,1'-biphenyl)-2-carboxylate

Supplier Sponsors

Name:[(2S,3R,4S,5S,6R)-2-[[(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-3H-pyrano[5,4-c]pyran-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
CAS Number: 21018-84-8Picture of molecule3D/inchi
FDA UNII:5L82GT5I0W
Nikkaji Web:J16.196I
XlogP3-AA:2.40 (est)
Molecular Weight:586.54770000
Formula:C29 H30 O13
NMR Predictor:Predict (works with chrome or firefox)
Category:flavoring agents
 
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
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 928.00 to 292.00 °C. @ 760.00 mm Hg (est)
Flash Point: 584.00 °F. TCC ( 306.67 °C. )
logP (o/w): 2.503 (est)
Soluble in:
 water, 99.5 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Flavor Type: bitter
bitter
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Amarogentin 95%
ExtraSynthese
For experimental / research use only.
Amarogentin
 
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
 
Safety in Use Information:
Category: flavoring agents
Recommendation for amarogentin usage levels up to:
 not for fragrance use.
 
 
Safety References:
EPI System: View
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :115149
National Institute of Allergy and Infectious Diseases:Data
[(2S,3R,4S,5S,6R)-2-[[(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-3H-pyrano[5,4-c]pyran-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
Chemidplus:0021018848
 
References:
 [(2S,3R,4S,5S,6R)-2-[[(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-3H-pyrano[5,4-c]pyran-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):115149
Pubchem (sid):135257526
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C09767
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
No odor group found for these
gentiana lutea root extract
FL/FR
prunus serotina bark extract
FL/FR
aldehydic
aldehydic
citronellyl oxyacetaldehyde
FL/FR
tridecanal
FL/FR
balsamic
peru balsam oil
FL/FR
peru balsam resinoid
FL/FR
terpinyl isovalerate
FL/FR
caramellic
fenugreek oleoresin
FL/FR
immortelle absolute
FL/FR
chocolate
cocoa hexenal
FL/FR
cocoa oleoresin
FL/FR
citrus
2-
heptanol
FL/FR
(+)-
nootkatone
FL/FR
bitter
orange peel oil brazil
FL/FR
cocoa
theobroma cacao extract
FL/FR
coffee
coffea arabica seed extract
FL/FR
roasted arabica
coffee bean oil
FL/FR
fatty
(E,Z,Z)-2,4,7-
tridecatrienal
FL/FR
floral
(Z)-
jasmone
FL/FR
nerol
FL/FR
terpinyl valerate
FL/FR
hay
tobacco leaf absolute
FL/FR
herbal
levisticum officinale root extract
FL/FR
incense
frankincense gum papyrifera
FL/FR
musk
dextro,laevo-
muscone
FL/FR
powdery
dibenzyl ketone
FL/FR
tea
camellia oleifera leaf extract
FL/FR
For Flavor
balsamic
peru balsam oil
FL/FR
peru balsam resinoid
FL/FR
bitter
2-
acetyl-5-methyl pyrrole
FL
cocoa pyrazines base (mixture of pyrazines)
FL
dibenzyl ketone
FL/FR
3,4-
dihydroxybenzaldehyde
FL
frankincense gum papyrifera
FL/FR
glyceryl tributyrate
FL
methyl ethoxypyrazine
FL
1,3-
octane diol
FL
paullinia cupana seed extract
FL
terpin anhydrous
FL
terpinyl isovalerate
FL/FR
theobromine
FL
(E,Z,Z)-2,4,7-
tridecatrienal
FL/FR
brown
fenugreek oleoresin
FL/FR
juglans nigra hulls extract
FL
juglans nigra shell extract
FL
chocolate
bittersweet
chocolate flavor
FL
bitter
chocolate flavor
FL
cocoa oleoresin
FL/FR
citrus
citronellyl oxyacetaldehyde
FL/FR
bitter
lemon flavor
FL
nerol
FL/FR
(+)-
nootkatone
FL/FR
bitter
orange flavor
FL
cocoa
cocoa distillates
FL
cocoa hexenal
FL/FR
theobroma cacao extract
FL/FR
coffee
coffea arabica seed extract
FL/FR
cooling
(2S,5R)-N-[4-(2-
amino-2-oxoethyl)phenyl]-5-methyl-2-(propan-2-yl)cyclohexanecarboxamide
FL
fruity
2-
heptanol
FL/FR
bitter
orange peel oil brazil
FL/FR
prunus serotina bark extract
FL/FR
terpinyl valerate
FL/FR
grassy
tobacco leaf absolute
FL/FR
green
gentiana lutea root extract
FL/FR
immortelle absolute
FL/FR
musk
dextro,laevo-
muscone
FL/FR
nutty
peanut oxazole
FL
roasted
acer spicatum bark extract
FL
roasted arabica
coffee bean oil
FL/FR
spicy
levisticum officinale root extract
FL/FR
sulfurous
2-
methyl thiophene
FL
tea
camellia oleifera leaf extract
FL/FR
waxy
tridecanal
FL/FR
woody
ginseng distillates
FL
(Z)-
jasmone
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 gentiana spp. root
Search Trop Picture
 gentian indian gentian
Search PMC Picture
 swertia spp.
Search Trop Picture
 
Synonyms:
[(2S,3R,4S,5S,6R)-2-[[(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-3H-pyrano[5,4-c]pyran-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
 sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester
2-(4aS-(4aalpha,5beta,6alpha))-3,3',5-trihydroxy-(1,1'-biphenyl)-2-carboxylate
 

Articles:

PubMed:Amelioration of oxidative and inflammatory changes by Swertia chirayita leaves in experimental arthritis.
PubMed:Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway.
PubMed:Amarogentin ameliorates diabetic disorders in animal models.
PubMed:Amarogentin Induces Apoptosis of Liver Cancer Cells via Upregulation of p53 and Downregulation of Human Telomerase Reverse Transcriptase in Mice.
PubMed:[Chemical constituents of Swertia patens].
PubMed:Chemotaxonomic Studies of Nine Gentianaceae Species from Western China Based on Liquid Chromatography Tandem Mass Spectrometry and Fourier Transform Infrared Spectroscopy.
PubMed:Chromatographic Evaluation and Characterization of Components of Gentian Root Extract Used as Food Additives.
PubMed:Phytochemical investigation of crude methanol extracts of different species of Swertia from Nepal.
PubMed:Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes.
PubMed:Receptor Polymorphism and Genomic Structure Interact to Shape Bitter Taste Perception.
PubMed:Chinese medicine amygdalin and β-glucosidase combined with antibody enzymatic prodrug system as a feasible antitumor therapy.
PubMed:Amarogentin regulates self renewal pathways to restrict liver carcinogenesis in experimental mouse model.
PubMed:Contents of therapeutic metabolites in Swertia chirayita correlate with the expression profiles of multiple genes in corresponding biosynthesis pathways.
PubMed:LC-ESI/MS determination of xanthone and secoiridoid glycosides from in vitro regenerated and in vivo Swertia chirayita.
PubMed:Detection of intermediates through high-resolution mass spectrometry for constructing biosynthetic pathways for major chemical constituents in a medicinally important herb, Swertia chirayita.
PubMed:Expression and functional activity of the bitter taste receptors TAS2R1 and TAS2R38 in human keratinocytes.
PubMed:Comparative HPLC/ESI-MS and HPLC/DAD study of different populations of cultivated, wild and commercial Gentiana lutea L.
PubMed:Amarogentin, a secoiridoid glycoside, abrogates platelet activation through PLC γ 2-PKC and MAPK pathways.
PubMed:The bitter barricading of prostaglandin biosynthesis pathway: understanding the molecular mechanism of selective cyclooxygenase-2 inhibition by amarogentin, a secoiridoid glycoside from Swertia chirayita.
PubMed:Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats.
PubMed:Inhibition of vascular smooth muscle cell proliferation by Gentiana lutea root extracts.
PubMed:Prevention of liver carcinogenesis by amarogentin through modulation of G1/S cell cycle check point and induction of apoptosis.
PubMed:Inhibition of aldose reductase by Gentiana lutea extracts.
PubMed:Phenolic-linked biochemical rationale for the anti-diabetic properties of Swertia chirayita (Roxb. ex Flem.) Karst.
PubMed:Inhibition of myeloperoxidase and antioxidative activity of Gentiana lutea extracts.
PubMed:Activity-guided isolation of antioxidant xanthones from Swertia chirayita (Roxb.) H. Karsten (Gentianaceae).
PubMed:The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin.
PubMed:Protocol for in vitro regeneration and marker glycoside assessment in Swertia chirata Buch-Ham.
PubMed:Assessment of systemic interaction between Swertia chirata extract and its Bioactive constituents in rabbits.
PubMed:Determination of gentisin, isogentisin, and amarogentin in Gentiana lutea L. by capillary electrophoresis.
PubMed:Simultaneous estimation of mangiferin and four secoiridoid glycosides in rat plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study of herbal preparation.
PubMed:Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS.
PubMed:Liquid chromatography/tandem mass spectrometric study and analysis of xanthone and secoiridoid glycoside composition of Swertia chirata, a potent antidiabetic.
PubMed:Amarogentin can reduce hyperproliferation by downregulation of Cox-II and upregulation of apoptosis in mouse skin carcinogenesis model.
PubMed:Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae).
PubMed:A sensitive and selective LC-MS-MS method for simultaneous determination of picroside-I and kutkoside (active principles of herbal preparation picroliv) using solid phase extraction in rabbit plasma: application to pharmacokinetic study.
PubMed:Evaluation of the anticarcinogenic activity of Swertia chirata Buch.Ham, an Indian medicinal plant, on DMBA-induced mouse skin carcinogenesis model.
PubMed:Production of amarogentin in root cultures of Swertia chirata.
PubMed:Synthesis of 3,3',5-trihydroxybiphenyl-2-carboxylic acid, a component of the bitterest natural product amarogentin and its coenzyme A and N-acetyl cysteamine thiol esters.
PubMed:Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms.
PubMed:Secoiridoids and xanthones from Gentianella nitida.
PubMed:Secoiridoid glucosides from Swertia mileensis.
PubMed:Amarogentin, a naturally occurring secoiridoid glycoside and a newly recognized inhibitor of topoisomerase I from Leishmania donovani.
PubMed:[Simultaneous determination of five bitter secoiridoid glycosides in nine Chinese Gentiana species used as the Chinese drug "long dan" by high performance liquid chromatography].
PubMed:Desorption/Chemical ionization mass spectrometry of bitter glycosides from gentiana1.
PubMed:[High-performance liquid-liquid chromatography in beverage analysis].
 
Notes:
secoiridoid glycoside.
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