dextro-(-)-quinic acid
cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (3R,5R)-
Identification
| Name | dextro-(-)-quinic acid |
| IUPAC | (3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid |
| CAS Number | 77-95-2 |
| EINECS | 201-072-8 |
| FDA UNII | 058C04BGYI |
| Molecular Formula | C7 H12 O6 |
| Molecular Weight | 192.16784000 |
| MDL Number | MFCD00003864 |
| Nikkaji Number | J9.262B |
| Beilstein | 2212412 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 162.50 °C. @ 760.00 mm Hg |
| Boiling Point | 438.42 °C. @ 760.00 mm Hg (est) |
| Flash Point | 452.00 °F. TCC ( 233.10 °C. ) (est) |
| logP (o/w) | -2.023 (est) |
| Soluble in | water, 2.90E+05 mg/L @ 9C (exp) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | buffering agents |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | subcutaneous-mouse LD50 10000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | buffering agents |
| Recommendation for dextro-(-)-quinic acid usage levels up to | not for fragrance use. |
| Recommendation for dextro-(-)-quinic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(-)-
chinasaure
(-)-
chinic acid
cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (3R,5R)-
(-)-
kinic acid
(-)-
quinic acid
D-(-)-
quinic acid
quinic acid natural
(-)-1,3,4,5-
tetrahydroxycyclohexane carboxylic acid
(1R-(1alpha,3alpha,4alpha,5beta)-1,3,4,5-
tetrahydroxycyclohexane carboxylic acid
(3R,5R)-1,3,4,5-
tetrahydroxycyclohexane-1-carboxylic acid
(1S,3R,4S,5R)-1,3,4,5-
tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-
tetrahydroxycyclohexanecarboxylic acid
1,3,4,5-
tetrahydroxycyclohexanecarboxylic acid (1R-(1alpha,3alpha,4alpha,5beta)
PubMed:
Heptanuclear antiferromagnetic Fe(III)-D-(-)-quinato assemblies with an S = 3/2 ground state-pH-specific synthetic chemistry, spectroscopic, structural, and magnetic susceptibility studies.
PubMed:
Medicinal flowers. XXXX . Structures of dihydroisocoumarin glycosides and inhibitory effects on aldose reducatase from the flowers of Hydrangea macrophylla var.thunbergii.
PubMed:
Structure- and dose-absorption relationships of coffee polyphenols.
PubMed:
Determination of α-hydroxy acids and their enantiomers in fruit juices by ligand exchange CE with a dual central metal ion system.
PubMed:
Mining the Sinorhizobium meliloti transportome to develop FRET biosensors for sugars, dicarboxylates and cyclic polyols.
PubMed:
Enantioseparation of α-hydroxy acids by chiral ligand exchange CE with a dual central metal ion system.
PubMed:
Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid.
PubMed:
Mechanism of change in enantiomer migration order of enantioseparation of tartaric acid by ligand exchange capillary electrophoresis with Cu(II) and Ni(II)-D-quinic acid systems.
PubMed:
Colonic availability of polyphenols and D-(-)-quinic acid after apple smoothie consumption.
PubMed:
Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors.
PubMed:
Hydrothermal synthesis and characterization of 2D M(II)-Quinate (M = Co,Zn) metal-organic lattice assemblies: solid-state solution structure correlation in M(II)-hydroxycarboxylate systems.
PubMed:
Enantioseparation of DL-isocitric acid by a chiral ligand exchange CE with Ni(II)-D-quinic acid system.
PubMed:
Metal(II)-ligand molar ratio dependence of enantioseparation of tartaric acid by ligand exchange CE with Cu(II) and Ni(II)-D-quinic acid systems.
PubMed:
pH-Dependent syntheses, structural and spectroscopic characterization, and chemical transformations of aqueous Co(II)-quinate complexes: an effort to delve into the structural speciation of the binary Co(II)-quinic acid system.
PubMed:
pH-specific synthetic chemistry and solution studies in the binary system of iron(III) with the alpha-hydroxycarboxylate substrate quinic acid: potential relevance to iron chemistry in plant fluids.
PubMed:
Synthesis of carbasugar C-1 phosphates via Pd-catalyzed cyclopropanol ring opening.
PubMed:
Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption.
PubMed:
Expeditious synthesis of tri- and tetrahydroxyazepanes from D-(-)-quinic acid as potent glycosidase inhibitors.
PubMed:
Determination of chlorogenic acid in rat plasma by high performance chromatography after peritoneal administration of compound Daqingye injection.
PubMed:
Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrate lactones-an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V protein.
PubMed:
HPLC determination and pharmacokinetics of chlorogenic acid in rabbit plasma after an oral dose of Flos Lonicerae extract.
PubMed:
Insulinomimetic zinc(II) complexes with natural products: in vitro evaluation and blood glucose lowering effect in KK-Ay mice with type 2 diabetes mellitus.
PubMed:
A new strategy towards the total synthesis of phenanthridone alkaloids: synthesis of (+)-2,7-dideoxypancratistatin as a model study.
PubMed:
Direct chiral resolution of tartaric acid in food products by ligand exchange capillary electrophoresis using copper(II)-D-quinic acid as a chiral selector.
PubMed:
Synthesis of clustered glycoside-antigen conjugates by two one-pot, orthogonal, chemoselective ligation reactions: scope and limitations.
PubMed:
Interaction of 3'-O-caffeoyl D-quinic acid with human serum albumin.
PubMed:
Identification of host-plant chemicals stimulating oviposition by swallowtail butterfly,Papilio protenor.
PubMed:
Purification and characterization of hydroxycinnamoyl D-glucose. Quinate hydroxycinnamoyl transferase in the root of sweet potato, Ipomoea batatas Lam.
PubMed:
1-N-acylation of gentamicin C1a by a cyclic, chiral gamma-amino-alpha-hydroxy acid related to the (S)-4-amino-2-hydroxybutyric acid.