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Quinic acid

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Name

Quinic acid

EINECS 201-072-8
CAS No. 77-95-2 Density 1.828 g/cm3
PSA 118.22000 LogP -2.32140
Solubility 400 g/l (20 °C )in water Melting Point 165-170 °C
Formula C7H12O6 Boiling Point 438.4 °C at 760 mmHg
Molecular Weight 192.169 Flash Point 233.1 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 22-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 77-95-2 (Quinic acid) Hazard Symbols IrritantXi
Synonyms

Cyclohexanecarboxylicacid, 1,3,4,5-tetrahydroxy-, (-)- (8CI);Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-,[1R-(1a,3a,4a,5b)]-;(-)-Quinic acid;D-(-)-Quinic acid;D-Quinic acid;Quinic acid, (-)-;

Article Data 44

Quinic acid Synthetic route

191916-39-9

methyl (-)-quinate

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With sodium hydroxide; water for 13h; Ambient temperature;100%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 5h;90%
Multi-step reaction with 4 steps
1: triethylamine / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 20 °C
3: sodium tetrahydroborate / ethanol / 0.67 h / -30 °C
4: hydrogenchloride / water / 1 h
View Scheme
135711-58-9

Methyl (1S,3R,4R,5R)-3-<(tert-Butyl)dimethylsilyloxy>-1,4,5-trihydroxycyclohexane-1-carboxylate

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With potassium hydroxide; acetic acid In tetrahydrofuran; water 1) 1 h, 2) 15 h, r.t.;90%
202650-88-2

3-caffeoylquinic acid

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With methanol; sodium hydroxide at 60℃; for 4h;88%
With 3percent HCl at 90℃; for 3h; Product distribution;
Multi-step reaction with 2 steps
1: palladium/charcoal; acetic acid / Hydrogenation
2: aqueous hydrochloric acid
View Scheme
202650-88-2

3-caffeoylquinic acid

A

331-39-5

caffeic acid

B

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
bei der Alkalispaltung;
212891-05-9

1,3-di-O-caffeoylquinic acid

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With sodium hydroxide
With barium dihydroxide
25514-46-9

(1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With sodium hydroxide
With hydrogenchloride
2280-44-6

D-Glucose

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
microbial construct AB2848aroD/pKD136/pTW8090A;25 mmol
With Escherichia coli QP1.1; pKD12138; standard fermentation medium In water at 33 - 37℃; for 48h; pH=7.0;

A

331-39-5

caffeic acid

B

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With water; unspecific esterase hydrolysis;
With water hydrolysis with unspecific esterase;
114687-85-3

5-O-p-coumaroylquinic acid methyl ester

A

7400-08-0

p-Coumaric Acid

B

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Heating;

3,5-di-O-galloyl quinic acid

77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With tannase In water at 37℃; for 6h;

Quinic acid Specification

The CAS register number of Quinic acid is 77-95-2. It also can be called as 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid; D-(-)-Quinic acid and the IUPAC name about this chemical is (3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylate. The molecular formula about this chemical is C7H12O6 and the molecular weight is 192.17. It belongs to the following product categories which include Chiral; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Asymmetric Synthesis; Chiral Resolution Reagents; Chiral Resolving Reagents and so on.

Physical properties about Quinic acid are: (1)# of Rule of 5 Violations: 1; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 6; (7)#H bond donors: 5; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 118.22Å2; (10)Index of Refraction: 1.687; (11)Molar Refractivity: 40.04 cm3; (12)Molar Volume: 105 cm3; (13)Polarizability: 15.87x10-24cm3; (14)Surface Tension: 139.5 dyne/cm; (15)Enthalpy of Vaporization: 80.25 kJ/mol; (16)Boiling Point: 438.4 °C at 760 mmHg; (17)Vapour Pressure: 1.58E-09 mmHg at 25°C.

The Quinic acid is an acid which is found in cinchona bark and elsewhere in plants. This chemical is used as an astringent, it is also thought to displace binding of the mu opioid receptor antagonist, however this acid was originally thought to be pharmacologically inactive.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and do not breathe dust, you also need to keep avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@H]1C[C@](O)(CC(O)[C@@H]1O)C(O)=O
(2)InChI: InChI=1/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
(3)InChIKey: AAWZDTNXLSGCEK-RKGSPJAZBM
(4)Std. InChI: 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
(5)Std. InChIKey: AAWZDTNXLSGCEK-RKGSPJAZSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 10gm/kg (10000mg/kg)   Zeitschrift fuer die Gesamte Experimentelle Medizin. Vol. 113, Pg. 536, 1944.

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