D-(-)-Quinic acid - ≥98% , CAS No.77-95-2

CAS: 77-95-2 Cat. No.: Q109705 Formula: C₇H₁₂O₆ Molecular Weight: 192.17 Beilstein Registry Number: 2212412 EC Number: 201-072-8

GRADE & PURITY ≥98%

Synonyms

NSC1115 | Quinic acid, United States Pharmacopeia (USP) Reference Standard | 4gui | MEGxp0_001735 | SCHEMBL23845421 | 1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid | BSPBio_003137 | Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3R,4

Storage

Room temperature

Shipped In

Normal

Overview

D-(-)-Quinic acid, a plant metabolite, is chiral building block used in multistep chemical synthesis of natural compounds.

D-(−)-Quinic acid can be used as:      
A chiral selector electrolyte along with copper(II) sulfate. This electrolyte is utilized in chiral resolution DL-tartaric acid by ligand-exchange capillary electrophoresis method.      
A starting material in the synthesis of stereoisomers of 3,4,6-trihydroxyazepanes, 7-hydroxymethyl-3,4,5-trihydroxyazepanes, and 3,4,5-trihydroxyazepanes, as potential inhibitors of glycosidase.        
A precursor for the preparation of trihydroxy piperidine derivatives and (+)-proto-quercitol glycosidase inhibitors.

Specifications

Synonyms

NSC1115 | Quinic acid, United States Pharmacopeia (USP) Reference Standard | 4gui | MEGxp0_001735 | SCHEMBL23845421 | 1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid | BSPBio_003137 | Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3R,4

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488180083
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180083
• Canonical Smiles: C1C(C(C(CC1(C(=O)O)O)O)O)O
• IUPAC Name: (3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
• InChIKey: AAWZDTNXLSGCEK-LNVDRNJUSA-N
• INCHI: 1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5?,7?/m1/s1
• Isomeric SMILES: C1[C@H](C([C@@H](CC1(C(=O)O)O)O)O)O
• WGK Germany: 3
• RTECS: GU8650000
• Molecular Weight: 192.17
• Beilstein: 2212412
• Reaxy-Rn: 2693888
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2693888&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Alcohols and polyols
        • Level5 Cyclic alcohols and derivatives
          • Level6 Cyclitols and derivatives
            • Level7 Quinic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Cyclic alcohols and derivatives - Cyclitols and derivatives
• Direct Parent: Quinic acids and derivatives
• Alternative Parents: Cyclohexanols Alpha hydroxy acids and derivatives Tertiary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Quinic acid - Cyclohexanol - Hydroxy acid - Alpha-hydroxy acid - Tertiary alcohol - Secondary alcohol - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

APP Tclin Amyloid-beta A4 protein (8510 Activities)

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MT2 (2907 Activities)

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A549 (127892 Activities)

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HepG2 (196354 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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Associated Targets(non-human)

Sele Selectin E (1 Activities)

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Selp P-selectin (7 Activities)

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pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: -43.5 ° (C=10, H2O)
• Melt Point(°C): 166-168°C
• Molecular Weight: 192.170 g/mol
• XLogP3: -2.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 192.063 Da
• Monoisotopic Mass: 192.063 Da
• Topological Polar Surface Area: 118.000 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 203.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1