| 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: | 21018-84-8 |  3D/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, Edge or firefox) |
Category:flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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 |
| Taste Description: very bitter |
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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 |
| AIDS Citations:Search |
| Cancer Citations:Search |
| 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:
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 |
black camellia sinensis leaf infusion
FL/FR |
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 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 |
| herbal |
black camellia sinensis leaf infusion
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:
Occurrence (nature, food, other): note
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]. |
|
