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Category: flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 928.00 to 292.00 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 584.00 °F. TCC ( 306.67 °C. )
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| logP (o/w): | 2.503 (est) |
| Soluble in: |
| | water, 99.5 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Flavor Type: bitter |
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| | bitter |
Taste Description:
| very bitter |
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
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| 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 | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | flavoring agents |
| Recommendation for amarogentin usage levels up to: | | | not for fragrance 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 : | 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 |
| | 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 |
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| 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 |
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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]. |
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