77-95-2 | D-(-)-Quinic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$18.00	$12.00
5g	98%	in stock	$46.00	$32.00
10g	98%	in stock	$47.00	$33.00
25g	98%	in stock	$105.00	$73.00
50g	98%	in stock	$162.00	$114.00
100g	98%	in stock	$300.00	$210.00

Description

• Catalog Number: AE04054
• Chemical Name: D-(-)-Quinic acid
• CAS Number: 77-95-2
• Molecular Formula: C7H12O6
• Molecular Weight: 192.16658000000004
• MDL Number: MFCD00003864
• SMILES: O[C@@H]1[C@H](O)C[C@@](C[C@H]1O)(O)C(=O)O

Computed Properties

• Complexity: 203
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 5
• Rotatable Bond Count: 1
• XLogP3: -2.4

Upstream Synthesis Route

The (1α,3R,4α,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid is a versatile compound widely utilized in chemical synthesis as a chiral building block. It plays a crucial role in the creation of complex molecules with specific stereochemical properties, making it highly valuable in the pharmaceutical and fine chemical industries. Its unique structure and reactivity allow for the selective manipulation of molecular chirality, enabling chemists to design and synthesize a diverse range of bioactive compounds and specialty chemicals.

Literature

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  Journal of agricultural and food chemistry 20070418

• Aleppo tannin: structural analysis and salivary amylase inhibition.

  Carbohydrate research 20070409

• Progress towards the total synthesis of trichodermamides A and B: construction of the oxazine ring moiety.

  Organic letters 20070315

• Synthetic macrolides that inhibit breast cancer cell migration in vitro.

  Journal of the American Chemical Society 20070307

• cis-decalins from quinic acid: toward a synthesis of branimycin.

  Organic letters 20070301

• Profiling the chlorogenic acids and other caffeic acid derivatives of herbal chrysanthemum by LC-MSn.

  Journal of agricultural and food chemistry 20070207

• Water extract of propolis and its main constituents, caffeoylquinic acid derivatives, exert neuroprotective effects via antioxidant actions.

  Life sciences 20070102

• Liquid chromatography/electrospray ionization tandem mass spectrometry profiling of compounds from the infusion of Byrsonima fagifolia Niedenzu.

  Rapid communications in mass spectrometry : RCM 20070101

• Preparative isolation and purification of dicaffeoylquinic acids from the Ainsliaea fragrans champ by high-speed counter-current chromatography.

  Phytochemical analysis : PCA 20070101

• Source density analysis of the human EEG after ingestion of a drink containing decaffeinated extract of green tea enriched with L-theanine and theogallin.

  Nutritional neuroscience 20070101

• Biosynthesis of chlorogenic acids in growing and ripening fruits of Coffea arabica and Coffea canephora plants.

  Zeitschrift fur Naturforschung. C, Journal of biosciences 20070101

• Enzymatic preparation of metabolic intermediates, 3-dehydroquinate and 3-dehydroshikimate, in the shikimate pathway.

  Bioscience, biotechnology, and biochemistry 20061201

• Antioxidant activity of caffeoyl quinic acid derivatives from the roots of Dipsacus asper Wall.

  Journal of ethnopharmacology 20061124

• Effect of total phenolics from Laggera alata on acute and chronic inflammation models.

  Journal of ethnopharmacology 20061124

• New polyphenol derivative in Ipomoea batatas tubers and its antioxidant activity.

  Journal of agricultural and food chemistry 20061115

• Quantitative determination of phenolic compounds in artichoke-based dietary supplements and pharmaceuticals by high-performance liquid chromatography.

  Journal of agricultural and food chemistry 20061115

• Choleretic effects of yarrow (Achillea millefolium s.l.) in the isolated perfused rat liver.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20061101

• Changes in organic acids and sugars during early stages of development of acidic and acidless citrus fruit.

  Journal of agricultural and food chemistry 20061018

• High shikimate production from quinate with two enzymatic systems of acetic acid bacteria.

  Bioscience, biotechnology, and biochemistry 20061001

• Isolation and genetic mapping of a Coffea canephora phenylalanine ammonia-lyase gene (CcPAL1) and its involvement in the accumulation of caffeoyl quinic acids.

  Plant cell reports 20060901

• Novel and efficient syntheses of (-)-methyl 4-epi-shikimate and 4,5-epoxy-quinic and -shikimic acid derivatives as key precursors to prepare new analogues.

  The Journal of organic chemistry 20060707

• Evolution in caffeoylquinic acid content and histolocalization during Coffea canephora leaf development.

  Annals of botany 20060701

• Bioassay-guided isolation of aldose reductase inhibitors from Artemisia dracunculus.

  Phytochemistry 20060701

• Characterization by LC-MS(n) of four new classes of p-coumaric acid-containing diacyl chlorogenic acids in green coffee beans.

  Journal of agricultural and food chemistry 20060614

• Chlorogenic acid attenuates hypertension and improves endothelial function in spontaneously hypertensive rats.

  Journal of hypertension 20060601

• [Advances in caffeoylquinic acid research].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060601

• A concise, enantioselective approach to (-)-quinic acid.

  Organic letters 20060511

• Microsphere-based protease assays and screening application for lethal factor and factor Xa.

  Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

• NMR metabolomics to revisit the tobacco mosaic virus infection in Nicotiana tabacum leaves.

  Journal of natural products 20060501

• The novel antioxidant 3-O-caffeoyl-1-methylquinic acid induces Nrf2-dependent phase II detoxifying genes and alters intracellular glutathione redox.

  Free radical biology & medicine 20060415

• Fast analysis of sugars, fruit acids, and vitamin C in sea buckthorn (Hippophaë rhamnoides L.) varieties.

  Journal of agricultural and food chemistry 20060405

• Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves.

  Molecular nutrition & food research 20060401

• Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.

  Journal of natural products 20060401

• Characterization by LC-MS(n) of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids.

  Journal of agricultural and food chemistry 20060322

• Characterization of the arom gene in Rhizoctonia solani, and transcription patterns under stable and induced hypovirulence conditions.

  Current genetics 20060301

• Anti-hyperglycemic Potential of Natural Products.

  Mini reviews in medicinal chemistry 20060301

• A water soluble extract from Uncaria tomentosa (Cat's Claw) is a potent enhancer of DNA repair in primary organ cultures of human skin.

  Phytotherapy research : PTR 20060301

• Phenolic acids in Fructus Xanthii and determination of contents of total phenolic acids in different species and populations of Xanthium in China.

  Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20060301

• Crystal structures of Helicobacter pylori type II dehydroquinase inhibitor complexes: new directions for inhibitor design.

  Journal of medicinal chemistry 20060223

• ILSMRs (intensifier of beta-lactam-susceptibility in methicillin-resistant Staphylococcus aureus) from Tara [Caesalpinia spinosa (Molina) Kuntze].

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20060201

• Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense.

  Planta medica 20060101

• Novel 2-alkyl-1alpha,25-dihydroxy-19-norvitamin D3: efficient synthesis with Julia olefination, evaluation of biological activity and development of new analyzing system for co-activator recruitment.

  Anticancer research 20060101

• A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals.

  Antiviral research 20051201

• Hypouricemic effects of acacetin and 4,5-o-dicaffeoylquinic acid methyl ester on serum uric acid levels in potassium oxonate-pretreated rats.

  Biological & pharmaceutical bulletin 20051201

• Identification of caffeoylquinic acid derivatives from Brazilian propolis as constituents involved in induction of granulocytic differentiation of HL-60 cells.

  Bioorganic & medicinal chemistry 20051015

• Antihypertensive effects of Brazilian propolis: identification of caffeoylquinic acids as constituents involved in the hypotension in spontaneously hypertensive rats.

  Biological & pharmaceutical bulletin 20051001

• Oxidative metabolism of 5-o-caffeoylquinic acid (chlorogenic acid), a bioactive natural product, by metalloporphyrin and rat liver mitochondria.

  European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20050901

• Enzymatic production of caffeic acid by koji from plant resources containing caffeoylquinic acid derivatives.

  Bioscience, biotechnology, and biochemistry 20050901

• Identification of new dicaffeoylquinic acids from Chrysanthemum morifolium and their antioxidant activities.

  Planta medica 20050901

• Sialyl Lewis(x) analogs based on a quinic acid scaffold as the fucose mimic.

  Bioorganic & medicinal chemistry letters 20050701

• Quinic acid derivatives as sialyl Lewis(x)-mimicking selectin inhibitors: design, synthesis, and crystal structure in complex with E-selectin.

  Journal of medicinal chemistry 20050630

• Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS(n).

  Journal of agricultural and food chemistry 20050518

• Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin f from a single enantiomer of quinic Acid.

  Journal of the American Chemical Society 20050427

• Benzene-free synthesis of catechol: interfacing microbial and chemical catalysis.

  Journal of the American Chemical Society 20050309

• Site-directed mutagenesis of the active site region in the quinate/shikimate 5-dehydrogenase YdiB of Escherichia coli.

  The Journal of biological chemistry 20050225

• Analgesic activity of di-caffeoylquinic acids from roots of Lychnophora ericoides (Arnica da serra).

  Journal of ethnopharmacology 20050115

• An active ingredient of Cat's Claw water extracts identification and efficacy of quinic acid.

  Journal of ethnopharmacology 20050115

• The predominant polyphenol in the leaves of the resurrection plant Myrothamnus flabellifolius, 3,4,5 tri-O-galloylquinic acid, protects membranes against desiccation and free radical-induced oxidation.

  The Biochemical journal 20050101

• Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20050101

• Quinate oxidation in Gluconobacter oxydans IFO3244: purification and characterization of quinoprotein quinate dehydrogenase.

  FEMS microbiology letters 20041215

• Characterization of cigarette tobacco by direct electrospray ionization-ion trap mass spectrometry (ESI-ITMS) analysis of the aqueous extract--a novel and simple approach.

  Journal of agricultural and food chemistry 20041201

• 4-Caffeoyl-1,5-quinide in roasted coffee inhibits [3H]naloxone binding and reverses anti-nociceptive effects of morphine in mice.

  Psychopharmacology 20041101

• Strong antihyperglycemic effects of water-soluble fraction of Brazilian propolis and its bioactive constituent, 3,4,5-tri-O-caffeoylquinic acid.

  Biological & pharmaceutical bulletin 20041101

• Unique biosynthesis of dehydroquinic acid?

  Bioorganic chemistry 20041001

• Flavonoids from artichoke (Cynara scolymus L.) up-regulate endothelial-type nitric-oxide synthase gene expression in human endothelial cells.

  The Journal of pharmacology and experimental therapeutics 20040901

• Synthesis of the epimer of pericosine B from (-)-quinic Acid.

  Chemical & pharmaceutical bulletin 20040901

• Deodorization with ku-ding-cha containing a large amount of caffeoyl quinic acid derivatives.

  Journal of agricultural and food chemistry 20040825

• Crystal structures of Staphylococcus aureus type I dehydroquinase from enzyme turnover experiments.

  Proteins 20040815

• Biophysical and kinetic analysis of wild-type and site-directed mutants of the isolated and native dehydroquinate synthase domain of the AROM protein.

  Protein science : a publication of the Protein Society 20040801

• Identification and quantification of caffeoylquinic acids and flavonoids from artichoke (Cynara scolymus L.) heads, juice, and pomace by HPLC-DAD-ESI/MS(n).

  Journal of agricultural and food chemistry 20040630

• L-Aspartate semialdehyde and a 6-deoxy-5-ketohexose 1-phosphate are the precursors to the aromatic amino acids in Methanocaldococcus jannaschii.

  Biochemistry 20040615

• Engineering plants with increased levels of the antioxidant chlorogenic acid.

  Nature biotechnology 20040601

• Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyltransferase affects phenylpropanoid biosynthesis.

  The Plant cell 20040601

• Mass spectrometry of 1,3- and 1,5-dicaffeoylquinic acids.

  Journal of mass spectrometry : JMS 20040401

• LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root bark of Fagara zanthoxyloides Lam.

  Phytochemistry 20040401

• Studies for the transformation of carbocycles into carbohydrates: approach toward the synthesis of higher sugar derivatives.

  Carbohydrate research 20040225

• Inhibition of apple polyphenol oxidase activity by procyanidins and polyphenol oxidation products.

  Journal of agricultural and food chemistry 20040114

• Effects of benzyl glucoside and chlorogenic acid from Prunus mume on adrenocorticotropic hormone (ACTH) and catecholamine levels in plasma of experimental menopausal model rats.

  Biological & pharmaceutical bulletin 20040101

• Cytoprotective effects of heme oxygenase-1 induction by 3-O-caffeoyl-1-methylquinic acid.

  Free radical biology & medicine 20040101

• Antioxidant properties of prunes (Prunus domestica L.) and their constituents.

  BioFactors (Oxford, England) 20040101

• Enzymic synthesis of 3-[3- 13C]dehydroquinic acid.

  Organic & biomolecular chemistry 20031007

• 3-dehydroquinate production by oxidative fermentation and further conversion of 3-dehydroquinate to the intermediates in the shikimate pathway.

  Bioscience, biotechnology, and biochemistry 20031001

• Novel enzymatic synthesis of 4-O-cinnamoyl quinic and shikimic acid derivatives.

  The Journal of organic chemistry 20030711

• Design, synthesis and evaluation of bifunctional inhibitors of type II dehydroquinase.

  Organic & biomolecular chemistry 20030621

• Changes in broccoli (Brassica oleracea L. Var. italica) health-promoting compounds with inflorescence development.

  Journal of agricultural and food chemistry 20030618

• Protective effects of quinic acid derivatives on tetrahydropapaveroline-induced cell death in C6 glioma cells.

  Biological & pharmaceutical bulletin 20030601

• Quinic acid induces hypovirulence and expression of a hypovirulence-associated double-stranded RNA in Rhizoctonia solani.

  Current genetics 20030501

• Inhibition of xanthine oxidase by phenolic conjugates of methylated quinic acid.

  Planta medica 20030501

• Antioxidant activity of galloyl quinic derivatives isolated from P. lentiscus leaves.

  Free radical research 20030401

• Quantitative evaluation of antioxidant components in prunes (Prunus domestica L.).

  Journal of agricultural and food chemistry 20030226

• Expression of a hypovirulence-causing double-stranded RNA is associated with up-regulation of quinic acid pathway and down-regulation of shikimic acid pathway in Rhizoctonia solani.

  Current genetics 20030201

• New developments in oxidative fermentation.

  Applied microbiology and biotechnology 20030201

• Synthesis of anellated carbasugars from (--)-quinic acid.

  Carbohydrate research 20030131

• Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism.

  The Journal of biological chemistry 20030103

• Effects of caffeoyl conjugates of isoprenyl-hydroquinone glucoside and quinic acid on leukocyte function.

  Life sciences 20021108

• Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus).

  Journal of agricultural and food chemistry 20021106

• Antimutagenicity of mono-, di-, and tricaffeoylquinic acid derivatives isolated from sweetpotato (Ipomoea batatas L.) leaf.

  Bioscience, biotechnology, and biochemistry 20021101

• Synthesis and mannose receptor-mediated uptake of clustered glycomimetics by human dendritic cells: effect of charge.

  Bioorganic & medicinal chemistry letters 20021007

• Vinyl fluoride as an isoelectronic replacement for an enolate anion: inhibition of type II dehydroquinases.

  Chemical communications (Cambridge, England) 20020907

• Inhibitory effects of plant phenols on the activity of selected enzymes.

  Journal of agricultural and food chemistry 20020605

• LC/MS/MS characterization of phenolic constituents in dried plums.

  Journal of agricultural and food chemistry 20020605

• Anthocyanins from flowers of Cichorium intybus.

  Phytochemistry 20020601

• Dicinnamoylquinides in roasted coffee inhibit the human adenosine transporter.

  European journal of pharmacology 20020510

• Study of the organic acids composition of quince (Cydonia oblonga Miller) fruit and jam.

  Journal of agricultural and food chemistry 20020410

• A new strategy towards the total synthesis of phenanthridone alkaloids: synthesis of (+)-2,7-dideoxypancratistatin as a model study.

  Chemical communications (Cambridge, England) 20020321

• Ilyobacter insuetus sp. nov., a fermentative bacterium specialized in the degradation of hydroaromatic compounds.

  International journal of systematic and evolutionary microbiology 20020301

• Propionivibrio limicola sp. nov., a fermentative bacterium specialized in the degradation of hydroaromatic compounds, reclassification of Propionibacter pelophilus as Propionivibrio pelophilus comb. nov. and amended description of the genus Propionivibrio.

  International journal of systematic and evolutionary microbiology 20020301

• Green coffee bean extract and its metabolites have a hypotensive effect in spontaneously hypertensive rats.

  Hypertension research : official journal of the Japanese Society of Hypertension 20020101

• Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods.

  Phytochemical analysis : PCA 20020101

• Benzene-free synthesis of hydroquinone.

  Journal of the American Chemical Society 20011107

• Hydroaromatic equilibration during biosynthesis of shikimic acid.

  Journal of the American Chemical Society 20011024

• Direct chiral resolution of tartaric acid in food products by ligand exchange capillary electrophoresis using copper(II)-D-quinic acid as a chiral selector.

  Journal of chromatography. A 20011012

• Novel hyperbranched glycomimetics recognized by the human mannose receptor: quinic or shikimic acid derivatives as mannose bioisosteres.

  Chembiochem : a European journal of chemical biology 20011001

• Two flavonoids and other compounds from the aerial parts of Centaurea bracteata from Italy.

  Phytochemistry 20010601

• Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei.

  Planta medica 20010601

• [Study on the structure and activity of new phenolic acid compounds from Erigeron breviscapus].

  Yao xue xue bao = Acta pharmaceutica Sinica 20010501

• Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.

  Journal of medicinal chemistry 19990211

• Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2.

  Journal of natural products 19981001

• Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.

  Antimicrobial agents and chemotherapy 19980101

• The anti-HIV activity and mechanisms of action of pure compounds isolated from Rosa damascena.

  Biochemical and biophysical research communications 19961204

• Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.

  Proceedings of the National Academy of Sciences of the United States of America 19960625

• Anti-AIDS agents, 1. Isolation and characterization of four new tetragalloylquinic acids as a new class of HIV reverse transcriptase inhibitors from tannic acid.

  Journal of natural products 19890101