dextro-(-)-quinic acid
cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (3R,5R)-
 
Notes:
an acid which is found in cinchona bark and elsewhere in plants. (from stedman, 26th ed) Occurs in coffee beans and many other plant sources. Food acidulant with good taste characteristics, use limited by cost Quinic acid is an organic acid which is found in cinchona bark and elsewhere in plants. More specifically, quinic acid is a crystalline acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, peaches, pears, plums, vegetables etc. Quinic acid and Shikimic acid are key intermediates in the biosynthesis of aromatic compounds in living systems. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.; Quinic acid, C7H12O6 is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee.; This acid is a versatile chiral starting material for the synthesis of new pharmaceuticals. A new medicament for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market recently.
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      Q0009 D-(-)-Quinic Acid >98.0%(T)
       
Synonyms   Articles   Notes   Search
(3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid (Click)
CAS Number: 77-95-2Picture of molecule
ECHA EINECS - REACH Pre-Reg: 201-072-8
FDA UNII: 058C04BGYI
Nikkaji Web: J9.262B
Beilstein Number: 2212412
MDL: MFCD00003864
XlogP3-AA: -2.40 (est)
Molecular Weight: 192.16784000
Formula: C7 H12 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: buffering agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: buffering agents
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Suppliers:
Carbosynth
For experimental / research use only.
D-(-)-Quinic Acid
ExtraSynthese
For experimental / research use only.
Quinic Acid
Penta International
QUINIC ACID NATURAL, Kosher
Penta International
QUINIC ACID, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
Quinic Acid 98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
D-(-)-Quinic Acid 98%
TCI AMERICA
For experimental / research use only.
D-(-)-Quinic Acid >98.0%(T)
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Safety Information:
Preferred SDS: View
 
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:
subcutaneous-mouse LD50 10000 mg/kg
Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 113, Pg. 536, 1944.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
EPI System: View
ClinicalTrials.gov: search
Daily Med: search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA GENetic TOXicology: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6508
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Chemidplus: 0000077952
RTECS: GU8650000 for cas# 77-95-2
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References:
 (3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 77-95-2
Pubchem (cid): 6508
Pubchem (sid): 134972808
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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
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C00296
HMDB (The Human Metabolome Database): HMDB03072
FooDB: FDB001170
Export Tariff Code: 2918.19.9000
MedlinePlusSupp: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 apricot fruit
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 banana fruit
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 bean mung bean seed
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 beet leaf
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 bilberry leaf
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 broccoli asparagus broccoli leaf
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 brussel sprout leaf
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 buckthorn sea buckthorn fruit
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 cabbage leaf
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 carrot root
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 celery root
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 cherry sour cherry fruit
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 chive leaf
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 coconut seed
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 coffee bean
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 corn plant
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 cranberry fruit
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 currant black currant leaf
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 fennel seed
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 fig fruit
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 ginkgo biloba leaf
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 gooseberry fruit
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 grape fruit
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 grape leaf
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 grape root
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 kiwi fruit
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 lime fruit
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 mandarin fruit
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 onion bulb
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 orange fruit
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 parsley root
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 pea seed
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 peach leaf
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 pear fruit
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 plum fruit
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 pomegranate fruit
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 pomegranate leaf
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 potato tuber
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 rice leaf
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 sunflower seed
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 tamarind fruit
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 tamarind seed
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 tea leaf
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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)
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Articles:
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.
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