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Quinic acid

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Identification
Molecular formula
C7H12O6
CAS number
77-95-2
IUPAC name
(3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
State
State

Quinic acid is typically in a solid, crystalline state at room temperature.

Melting point (Celsius)
168.00
Melting point (Kelvin)
441.15
Boiling point (Celsius)
365.10
Boiling point (Kelvin)
638.30
General information
Molecular weight
192.17g/mol
Molar mass
192.1710g/mol
Density
1.7400g/cm3
Appearence

Quinic acid appears as a white, crystalline solid. It is often found as colorless, transparent crystals.

Comment on solubility

Solubility Insights for (3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid

The solubility of (3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid can be understood through several key factors:

  • Polarity: This compound is rich in hydroxyl (–OH) groups, which enhances its polarity. The presence of multiple hydroxyl groups means that the compound can form hydrogen bonds with water, leading to a higher aqueous solubility.
  • Hydrogen Bonding: The capacity for intramolecular and intermolecular hydrogen bonding plays a significant role. These interactions promote solvation processes, enhancing its solubility in polar solvents like water.
  • Structural Influence: The cyclic structure of the compound may contribute to its solubility characteristics. The arrangement of the hydroxyl groups on the cyclohexane ring can facilitate interaction with solvent molecules.
  • Temperature Effects: As with many organic compounds, the solubility of (3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid can increase with temperature. Higher temperatures can help to break intermolecular interactions and improve solvation.

In summary, one can expect (3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid to show good solubility in water owing to its hydroxyl functional groups fostering strong hydrogen bonding capabilities. Its behavior in organic solvents or mixtures may vary based on their polarity, indicating a complex solubility profile that warrants consideration in practical applications.

Interesting facts

Interesting Facts about (3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid

(3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid, often referred to in short as THCA, is a fascinating compound that belongs to the class of cyclohexane derivatives. Here are some highlights about this intriguing chemical:

  • Stereo-specificity: The designation of (3R,5R) indicates that THCA has specific stereochemistry, which is crucial in determining its biological activity and how it interacts with other molecules.
  • Applications: This compound has potential applications in pharmaceutical chemistry. Its hydroxyl groups may play a critical role in modulating the activity of certain enzymes and receptors, making it a point of interest in drug design.
  • Natural Occurrence: While this compound can be synthesized in the laboratory, it might also be derived from natural sources, showcasing how mother nature often inspires synthetic pathways.
  • Functional Versatility: The presence of multiple hydroxyl groups (-OH) makes this compound a valuable intermediate in organic synthesis, as these groups can participate in hydrogen bonding and contribute to solubility in biological systems.
  • Potential as a Building Block: THCA can serve as a building block for more complex organic molecules, facilitating the development of new materials and compounds in various fields from medicine to materials science.

In conclusion, (3R,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid is not only a complex molecule due to its rich hydroxy and carboxylic functionalities but also a significant player in the world of chemistry, paving the way for innovative advancements in various applications.

Synonyms
quinic acid
77-95-2
D-(-)-Quinic acid
(-)-quinic acid
quinate
Chinic acid
Kinic acid
Chinasaure
D-QUINIC ACID
D(-)-Quinic acid
L-Quinic acid
L-Quinate
MFCD00003864
(3r,5r)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Rel-Quinic Acid
CHEBI:17521
NSC1115
SpecPlus_000419
NSC59258
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
(-)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
DivK1c_006515
058C04BGYI
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (-)-
NSC-59258
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1R-(1-alpha,3-alpha,4-alpha,5-beta))-
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-
SDCCGMLS-0066613.P001
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid (1R-(1alpha,3alpha,4alpha,5beta)
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1theta-(1alpha,3alpha,4alpha,5beta))-
1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid
Quinicacid
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1alpha,3R,4alpha,5R)-
D-(-)-Kinic Acid
D-(-)-Chinic Acid
EINECS 201-072-8
NSC 59258
UNII-058C04BGYI
Chinate
Kinate
1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylate
4gui
4iuo
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3R,4.alpha.,5R)-
(-)Quinic acid
Quinic acid, D-
QIC
D-(-)-Quinic-acid
Spectrum_001413
Spectrum2_001790
Spectrum3_001349
Spectrum4_001867
Spectrum5_000434
QUINIC ACID [MI]
bmse000306
SCHEMBL39556
BSPBio_003137
KBioGR_002336
KBioSS_001893
SPECTRUM310018
MLS002207201
QUINIC ACID [USP-RS]
QUINIC ACID [WHO-DD]
SPBio_001719
CHEMBL465398
MEGxp0_001735
SCHEMBL1286207
SCHEMBL1286208
SCHEMBL7923331
D-(-)-Quinic acid, 98%
SCHEMBL23845421
ACon1_001963
CHEBI:26490
D-(-)-Quinic acid (Standard)
HY-N0464R
KBio1_001459
KBio2_001893
KBio2_004461
KBio2_007029
KBio3_002357
DTXSID70998288
HMS3885A12
HY-N0464
NSC-1115
BBL033519
BDBM50485632
CCG-38438
s3886
STK801928
(-) Quinic acid, analytical standard
AKOS005622501
FQ15911
NCGC00178246-01
NCGC00178246-02
1ST40055
BP-12304
DA-62619
PD087258
SMR001306762
VS-12119
CS-0008991
Q0009
C00296
D-(-)-Quinic acid, purum, >=98.0% (T)
EN300-197153
H10089
Q424931
883DE888-EC82-454C-B69C-8B1F9AC6DAA9
Z1255382952
(1R,3R,4R,5R)-(-)-Tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylicacid
(1|A,3R,4|A,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-tetrakis(oxidanyl)cyclohexane-1-carboxylic acid
Quinic acid, United States Pharmacopeia (USP) Reference Standard
(-)-QUINIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
(1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
Quinic Acid, Pharmaceutical Secondary Standard; Certified Reference Material
Cyclohexanecarboxylic acid,3,4,5-tetrahydroxy-, (1.alpha.,3.alpha.,4.alpha.,5.beta.)-
7729-33-1
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha., 3.alpha.,4.alpha.,5.beta.)-