loganic acid

(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

CAS: 22255-40-9 C16 H24 O10 MW: 376.35928000

Identification

Nameloganic acid
CAS Number22255-40-9
EINECS244-875-9
FDA UNIISearch
Molecular FormulaC16 H24 O10
Molecular Weight376.35928000
MDL NumberMFCD00017417
Nikkaji NumberJ15.893C
Beilstein4887090

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 646.26 °C. @ 760.00 mm Hg (est)
Flash Point 456.00 °F. TCC ( 235.60 °C. ) (est)
logP (o/w) -2.411 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for loganic acid usage levels up tonot for fragrance use.
Recommendation for loganic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

gentiana straminea

Synonyms

(1S,4aS,6S,7R,7aS)-6-hydroxy-7- methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid PubMed: [Content of gentiopicroside and loganic acid in Radix gentianae and their fingerprints]. PubMed: [Content determination of loganic acid and gentiopicroside in Tebitan herbal medicines Gentiana macrophylla and G. straminea by HPLC]. PubMed: Spatial variation profiling of four phytochemical constituents in Gentiana straminea (Gentianaceae). PubMed: Rapid preparative separation of six bioactive compounds from Gentiana crassicaulis Duthie ex Burk. using microwave-assisted extraction coupled with high-speed counter-current chromatography. PubMed: Effect of alkali metal cationization and multiple alkali metal exchange on the collision-induced dissociation of loganic acid studied by electrospray ionization tandem mass spectrometry PubMed: Anti-inflammatory effect of three iridoids in human neutrophils. PubMed: A novel lactone from Tripterospermum chinense. PubMed: S-Adenosyl-L-methionine: loganic acid methyltransferase. A carboxyl-alkylating enzyme from Vinca rosea. PubMed: Carboxyl group methylation of loganic acid by a cell-free enzyme preparation from Vinca rosea. PubMed: Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis. PubMed: Enzymic synthesis of loganin by carboxyl group methylation of loganic acid. PubMed: Two novel secoiridoid glucosides from Tripterospermum chinense. PubMed: Comparative study on "long-dan", "qin-jiao" and their adulterants by HPLC analysis. PubMed: Metabolic discrimination of Swertia mussotii and Swertia chirayita known as "Zangyinchen" in traditional Tibetan medicine by (1)H NMR-based metabolomics. PubMed: Simultaneous determination of six index constituents and comparative analysis of four ethnomedicines from genus Gentiana using a UPLC-UV-MS method. PubMed: Bioactive compounds from Cornus officinalis fruits and their effects on diabetic nephropathy. PubMed: Unexpected secoiridoid glucosides from Manulea corymbosa. PubMed: [Simultaneous determination of five iridoids in gentianae macrophyllae radix and their local variety by HPLC]. PubMed: Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats. PubMed: [Efficient method for analyzing absorbed ingredients of traditional Chinese medicine genitana macrophyllae radix]. PubMed: Analysis of iridoids, secoiridoids and xanthones in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea using LC-MS and RP-HPLC. PubMed: [Studies on the chemical constituents from stems and leaves of Lonicera macranthoides]. PubMed: Induction of apoptosis in human pancreatic MiaPaCa-2 cells through the loss of mitochondrial membrane potential (ΔΨm) by Gentiana kurroo root extract and LC-ESI-MS analysis of its principal constituents. PubMed: A simple method to identify the unprocessed Strychnos seeds used in herbal medicinal products. PubMed: [Determination of five active constituents in aerial part of Tibetan medicine Gentiana straminea by HPLC]. PubMed: A new iridoid glycoside and potential MRB inhibitory activity of isolated compounds from the rhizomes of Cyperus rotundus L. PubMed: UPLC-TOF-MS Characterization and Identification of Bioactive Iridoids in Cornus mas Fruit. PubMed: Coumarin glycosides and iridoid glucosides with neuroprotective effects from Hydrangea paniculata. PubMed: Phytochemical analysis of Plantago sempervirens from Majella National Park. PubMed: [Chemical constituents of glucoside fraction from Liuwei Dihuang Gantang]. PubMed: The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites. PubMed: A new iridoid glycoside from the roots of Dipsacus asper. PubMed: Lamiridosins, hepatitis C virus entry inhibitors from Lamium album. PubMed: Concentrations of the active constituents of the Tibetan folk medicine Qinjiao (Gentiana sect. Cruciata) within and between taxonomic species across the Qinghai-Tibetan Plateau. PubMed: Iridoid and phenylethanoid glucosides from Veronica lavaudiana. PubMed: Simultaneous determination of four iridoid and secoiridoid glycosides and comparative analysis of Radix Gentianae Macrophyllae and their related substitutes by HPLC. PubMed: [Studies on glycosides from Gentiana veitchiorum]. PubMed: Iridoidal glucosides from Gentiana rhodantha. PubMed: Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique. PubMed: 2,4-D and alkaloid accumulation in periwinkle cell suspensions. PubMed: The leaf epidermome of Catharanthus roseus reveals its biochemical specialization. PubMed: Iridoids from Spathodea campanulata P. Beauvais leaves. PubMed: Iridoids from Gentiana loureirii. PubMed: A comparative chemotaxonomic study on Vinca sardoa steam and Vinca difformis pourret. PubMed: Iridoid glucosides from Strychnos nux-vomica. PubMed: Iridoids and secoiridoids from Guettarda platypoda. PubMed: Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS. PubMed: Iridoids from Lippia graveolens. PubMed: Iridoid glycosides of Leonurus persicus. PubMed: An iridoid glucoside from dipsacus asperoides. PubMed: 4'-P-Coumaroyl Iridoid Glucosides from Gentiana pedicellata. PubMed: Iridoidic pattern in endemic Sardinian plants: the case of Galium species. PubMed: [Studies on chemical constituents of Eriophyton wallichii]. PubMed: Phenylethanoid and iridoid glycosides from the Thai medicinal plant, Barleria strigosa. PubMed: Chemistry of plants from Crete: stachyspinoside, a new flavonoid glycoside and iridoids from Stachys spinosa. PubMed: Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles. PubMed: Iridoids from Loasa acerifolia. PubMed: Secoiridoid glycosides and an antifungal anthranilate derivative from Gentiana tibetica. PubMed: Structural considerations on the iridoids as anti-inflammatory agents. PubMed: Effect of terpenoid precursor feeding and elicitation on formation of indole alkaloids in cell suspension cultures of Catharanthus roseus. PubMed: Studies on lens-aldose-reductase inhibitor in medicinal plants. II. Active constituents of Monochasma savatierii Franch. et Maxim. PubMed: Iridoids from Scaevola racemigera1. PubMed: Senburiside II, a New Iridoid Glucoside from Swertia japonica. PubMed: Iridoids from Scutellaria albida ssp. albida. PubMed: Isolation of iridoid and secoiridoid glycosides and comparative study on Radix gentianae and related adulterants by HPLC analysis. PubMed: Metabolic discrimination of Catharanthus roseus leaves infected by phytoplasma using 1H-NMR spectroscopy and multivariate data analysis. PubMed: Iridoids from seeds of Gentiana lutea. PubMed: Cantleyoside-dimethyl-acetal and other iridoid glucosides from Pterocephalus perennis--antimicrobial activities. PubMed: Iridoid glycosides from Gmelina philippensis. PubMed: Inerminosides A and B, two novel complex iridoid glycosides from Clerodendrum inerme. PubMed: A Secoiridoid Glucoside from Gentiana scabra var. buergeri. PubMed: Iridoid Glucoside of Swertia japonica.