Quinic acid supplier | CasNO.77-95-2

Name
Quinic acid
EINECS 201-072-8
CAS No. 77-95-2
Article Data44
CAS DataBase
Density 1.828 g/cm³
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
Appearance white to light yellow crystal powder
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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, (-)-;
PSA 118.22000
LogP -2.32140

Synthetic route

: 191916-39-9
methyl (-)-quinate

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
bei der Alkalispaltung;

: 212891-05-9
1,3-di-O-caffeoylquinic acid

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide
With hydrogenchloride

: 2280-44-6
D-Glucose

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
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;

: 2450-53-5, 16758-05-7, 89919-61-9, 89919-62-0, 101222-97-3
3,5-dicaffeoylquinic acid

A: 331-39-5
caffeic acid

B: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
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

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

: 3,5-di-O-galloyl quinic acid

: 77-95-2
D-(-)-quinic acid

Conditions

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

: herbacetin 7-O-(6''-quinylglucoside)

A: 77-95-2
D-(-)-quinic acid

B: 527-95-7
herbacetin

Conditions

Conditions	Yield
With hydrogenchloride In water

: 74-90-8
hydrogen cyanide

: 34315-08-7
Acetic acid (2R,6R)-2,6-diacetoxy-4-methylene-cyclohexyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multistep reaction;

: 2280-44-6
D-Glucose

A: 138-59-0
shikimic acid

B: 77-95-2
D-(-)-quinic acid

C: 2922-42-1
(-)-3-dehydroshikimic acid

Conditions

Conditions	Yield
With E. coli SP1.1; pKD12112 for 12h; Product distribution; var. time;
With air; Escherichia coli SP1.1PTS-; pSC6.090B at 33℃; for 60h; pH=7;
With air; Escherichia coli SP1.1PTS-; pSC6.090B at 33℃; for 30h; pH=7;

...Expand

5-dihydro-quinic acid: 5-dihydro-quinic acid

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
With ethanol; platinum Hydrogenation;

: 2280-44-6
D-Glucose

: 138-08-9
phosphoenolpyruvic acid

A: 138-59-0
shikimic acid

B: 77-95-2
D-(-)-quinic acid

C: 2922-42-1
(-)-3-dehydroshikimic acid

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; E. coli SP1.1; pKD12138; citric acid In water at 33℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;

...Expand

: 171824-23-0
(-)-(1S,4R,4aS,5R,8aR)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8a-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 86 percent / NaH / tetrahydrofuran / 23 h / Ambient temperature 2: 90 percent / O2, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature 3: 100 percent / pyridine / 38 h / Ambient temperature 4: 100 percent / diphenyl ether / 1 h / 280 °C 5: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 6: PPTS / 65 h 7: NaBH4 / methanol / 1.5 h / -78 °C 8: 100 percent / 14 h / 50 °C 9: 80 percent / Bu3SnH / toluene / 9 h / Heating 10: 86 percent / CBr4, MeOH / 19 h / Heating 11: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 11 steps
1: 86 percent / NaH / tetrahydrofuran / 23 h / Ambient temperature
2: 90 percent / O2, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature
3: 100 percent / pyridine / 38 h / Ambient temperature
4: 100 percent / diphenyl ether / 1 h / 280 °C
5: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C
6: PPTS / 65 h
7: NaBH4 / methanol / 1.5 h / -78 °C
8: 100 percent / 14 h / 50 °C
9: 80 percent / Bu3SnH / toluene / 9 h / Heating
10: 86 percent / CBr4, MeOH / 19 h / Heating
11: 100 percent / NaOH, H2O / 13 h / Ambient temperature
View Scheme

: 215929-06-9
(1R,4S,4aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-1,4,4a,7,8,8a-hexahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 90 percent / O2, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature 2: 100 percent / pyridine / 38 h / Ambient temperature 3: 100 percent / diphenyl ether / 1 h / 280 °C 4: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 5: PPTS / 65 h 6: NaBH4 / methanol / 1.5 h / -78 °C 7: 100 percent / 14 h / 50 °C 8: 80 percent / Bu3SnH / toluene / 9 h / Heating 9: 86 percent / CBr4, MeOH / 19 h / Heating 10: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 10 steps
1: 90 percent / O2, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature
2: 100 percent / pyridine / 38 h / Ambient temperature
3: 100 percent / diphenyl ether / 1 h / 280 °C
4: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C
5: PPTS / 65 h
6: NaBH4 / methanol / 1.5 h / -78 °C
7: 100 percent / 14 h / 50 °C
8: 80 percent / Bu3SnH / toluene / 9 h / Heating
9: 86 percent / CBr4, MeOH / 19 h / Heating
10: 100 percent / NaOH, H2O / 13 h / Ambient temperature
View Scheme

: 215929-09-2
(1R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 2: PPTS / 65 h 3: NaBH4 / methanol / 1.5 h / -78 °C 4: 100 percent / 14 h / 50 °C 5: 80 percent / Bu3SnH / toluene / 9 h / Heating 6: 86 percent / CBr4, MeOH / 19 h / Heating 7: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 215929-07-0
(1R,4S,4aR,6R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-5-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 100 percent / pyridine / 38 h / Ambient temperature 2: 100 percent / diphenyl ether / 1 h / 280 °C 3: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 4: PPTS / 65 h 5: NaBH4 / methanol / 1.5 h / -78 °C 6: 100 percent / 14 h / 50 °C 7: 80 percent / Bu3SnH / toluene / 9 h / Heating 8: 86 percent / CBr4, MeOH / 19 h / Heating 9: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 9 steps
1: 100 percent / pyridine / 38 h / Ambient temperature
2: 100 percent / diphenyl ether / 1 h / 280 °C
3: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C
4: PPTS / 65 h
5: NaBH4 / methanol / 1.5 h / -78 °C
6: 100 percent / 14 h / 50 °C
7: 80 percent / Bu3SnH / toluene / 9 h / Heating
8: 86 percent / CBr4, MeOH / 19 h / Heating
9: 100 percent / NaOH, H2O / 13 h / Ambient temperature
View Scheme

: 215929-14-9
(3aR,5S,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / CBr4, MeOH / 19 h / Heating 2: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 215929-12-7
(3aR,4S,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / 14 h / 50 °C 2: 80 percent / Bu3SnH / toluene / 9 h / Heating 3: 86 percent / CBr4, MeOH / 19 h / Heating 4: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 215929-11-6
(3aS,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: NaBH4 / methanol / 1.5 h / -78 °C 2: 100 percent / 14 h / 50 °C 3: 80 percent / Bu3SnH / toluene / 9 h / Heating 4: 86 percent / CBr4, MeOH / 19 h / Heating 5: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 215929-08-1
(1R,4S,4aR,6R,8R,8aS)-6-Acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-5-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / diphenyl ether / 1 h / 280 °C 2: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 3: PPTS / 65 h 4: NaBH4 / methanol / 1.5 h / -78 °C 5: 100 percent / 14 h / 50 °C 6: 80 percent / Bu3SnH / toluene / 9 h / Heating 7: 86 percent / CBr4, MeOH / 19 h / Heating 8: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 215929-13-8
(3aS,4S,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-4-(imidazole-1-carbothioyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / Bu3SnH / toluene / 9 h / Heating 2: 86 percent / CBr4, MeOH / 19 h / Heating 3: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 215929-10-5
(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: PPTS / 65 h 2: NaBH4 / methanol / 1.5 h / -78 °C 3: 100 percent / 14 h / 50 °C 4: 80 percent / Bu3SnH / toluene / 9 h / Heating 5: 86 percent / CBr4, MeOH / 19 h / Heating 6: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

: 138-59-0
shikimic acid

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 78 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C 3: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating 4: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h 5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 6: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme
Multi-step reaction with 8 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 83 percent / TsOH / CH2Cl2 / 1.5 h / Ambient temperature 3: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 4: 70 percent / HCl / methanol; H2O / 0.25 h 5: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature 6: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 7: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 8: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

Yield

Multi-step reaction with 7 steps
1: methanol; diethyl ether / -20 - -15 °C
2: 78 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C
3: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating
4: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h
5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature
6: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr
7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t.
View Scheme

Multi-step reaction with 8 steps
1: methanol; diethyl ether / -20 - -15 °C
2: 83 percent / TsOH / CH2Cl2 / 1.5 h / Ambient temperature
3: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature
4: 70 percent / HCl / methanol; H2O / 0.25 h
5: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature
6: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature
7: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr
8: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t.
View Scheme

: 40983-58-2
methyl shikimate

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 78 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C 2: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating 3: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h 4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 5: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 6: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme
Multi-step reaction with 7 steps 1: 83 percent / TsOH / CH2Cl2 / 1.5 h / Ambient temperature 2: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 3: 70 percent / HCl / methanol; H2O / 0.25 h 4: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature 5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 6: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

Yield

Multi-step reaction with 6 steps
1: 78 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C
2: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating
3: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h
4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature
5: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr
6: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t.
View Scheme

Multi-step reaction with 7 steps
1: 83 percent / TsOH / CH2Cl2 / 1.5 h / Ambient temperature
2: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature
3: 70 percent / HCl / methanol; H2O / 0.25 h
4: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature
5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature
6: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr
7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t.
View Scheme

: 101906-39-2
Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating 2: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h 3: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 4: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 5: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

Yield

Multi-step reaction with 5 steps
1: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating
2: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h
3: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature
4: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr
5: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t.
View Scheme

: 91758-24-6, 135711-52-3, 135711-63-6
Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate

: 77-95-2
D-(-)-quinic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 2: 70 percent / HCl / methanol; H2O / 0.25 h 3: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature 4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 5: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 6: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

Yield

Multi-step reaction with 6 steps
1: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature
2: 70 percent / HCl / methanol; H2O / 0.25 h
3: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature
4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature
5: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr
6: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t.
View Scheme

: 77-95-2
D-(-)-quinic acid

: 665-27-0
1,5-quinide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 24h; Heating;	100%
With Amberlyst (R) 15 ion-exchange resin In N,N-dimethyl-formamide; benzene for 16h; Heating;	99%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene for 12h; Reflux;	99%

: 67-56-1
methanol

: 77-95-2
D-(-)-quinic acid

: 191916-39-9
methyl (-)-quinate

Conditions

Conditions	Yield
With Amberlite IR 120 for 7h; Heating;	100%
With sulfuric acid at 20℃;	100%
With hydrogenchloride at 60℃; for 6h;	100%

: 77-95-2
D-(-)-quinic acid

: 67-64-1
acetone

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Conditions

Conditions	Yield
With sulfuric acid; sodium sulfate for 1h; Heating;	100%
With toluene-4-sulfonic acid; 2,2-dimethoxy-propane	94%
With toluene-4-sulfonic acid at 56℃; for 48h; Molecular sieve;	93%

: 77-95-2
D-(-)-quinic acid

: 431-03-8
dimethylglyoxal

: 149-73-5
trimethyl orthoformate

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In methanol for 16h; Heating;	99%
With camphor-10-sulfonic acid In methanol for 16h; Heating;	99%
With (1S)-10-camphorsulfonic acid In methanol for 19h; Reflux; Inert atmosphere;	99%

...Expand

: 77-95-2
D-(-)-quinic acid

: 108-94-1
cyclohexanone

: 35949-53-2
(-)-4,5-cyclohexylidenequinic acid lactone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 5h; Heating;	98%
With phosphoric acid for 0.75h; Heating;	87%
With sulfuric acid for 1h; Heating;	85%

: 77-95-2
D-(-)-quinic acid

: 108-24-7
acetic anhydride

: 32469-24-2
(1R,3R,4R,5R)-(-)-quinic acid tetraacetate

Conditions

Conditions	Yield
With dmap In pyridine for 24h; Ambient temperature;	98%
With pyridine Ambient temperature;	98%
With pyridine; dmap at 5℃; for 12h;	97%

: 77-95-2
D-(-)-quinic acid

: 108-94-1
cyclohexanone

: C13H18O5

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 7h; Heating;	98%

: 77-95-2
D-(-)-quinic acid

: 77-76-9
2,2-dimethoxy-propane

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone for 1h; Reflux;	98%
Stage #1: D-(-)-quinic acid With Amberlyst 15 In acetonitrile for 48h; Reflux; Inert atmosphere; Stage #2: 2,2-dimethoxy-propane In acetonitrile for 3h; Reflux; Inert atmosphere;	98%
With toluene-4-sulfonic acid In acetone for 7h; Reflux;	92%

: 77-95-2
D-(-)-quinic acid

: 67-64-1
acetone

: C10H14O5

Conditions

Conditions	Yield
With sulfuric acid at 100℃; for 0.0833333h; Microwave irradiation;	98%

: 77-95-2
D-(-)-quinic acid

: 100-52-7
benzaldehyde

: 216662-57-6
(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 19h; Heating;	97%
With toluene-4-sulfonic acid In toluene for 16h; Reflux;	92%
With toluene-4-sulfonic acid In toluene Heating;	84%

: 75-77-4
chloro-trimethyl-silane

: 77-95-2
D-(-)-quinic acid

: 364628-95-5
Trimethylsilyltetra-O-trimethylsilylchinat

Conditions

Conditions	Yield
With triethylamine at 0℃; for 4.5h;	95%

: 77-95-2
D-(-)-quinic acid

: 96-22-0
pentan-3-one

: 374687-78-2
3,4-O-ethylpropylidenequinic acid-1,5-lactone

Conditions

Conditions	Yield
With phosphoric acid at 180℃; for 12h;	94%
With toluene-4-sulfonic acid In toluene for 5h; Heating;	68%
With phosphoric acid for 12h; Reflux;	25 %Chromat.

: 463-82-1
2,2-dimethylpropane

: 77-95-2
D-(-)-quinic acid

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethyl acetate at 0 - 78℃; for 12h;	92%

: 672953-05-8
N,N,N',N''-tetrahexyl-N'',N''-dimethylguanidinium chloride

: 77-95-2
D-(-)-quinic acid

: 902493-71-4
C7H11O6(1-)*C27H58N3(1+)

Conditions

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane at 20℃; for 24h;	91%

: 77-95-2
D-(-)-quinic acid

: 108-24-7
acetic anhydride

: 64-19-7
acetic acid

: 32469-24-2
(1R,3R,4R,5R)-(-)-quinic acid tetraacetate

Conditions

Conditions	Yield
With perchloric acid at 20 - 60℃;	91%
With perchloric acid at 50 - 60℃; for 12h;

...Expand

: 77-95-2
D-(-)-quinic acid

: 100-52-7
benzaldehyde

: 32384-44-4
(1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	90%
With toluene-4-sulfonic acid In benzene Heating; Inert atmosphere;	89%

: 77-95-2
D-(-)-quinic acid

: 67-64-1
acetone

: 130474-38-3
3,4-isopropylidenequinide

Conditions

Conditions	Yield
With hydrogen cation for 16h; Ambient temperature;	90%
With hydrogen cation

: 77-95-2
D-(-)-quinic acid

: 95639-53-5
3(R),5(R)-trihydroxycyclohexanone

Conditions

Conditions	Yield
With oxygen; potassium hydroxide; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 18h; Sealed tube; Irradiation;	90%
With sulfuric acid In water at 20℃; for 3h;	76%
With sodium hypochlorite solution; sulfuric acid In water at 20℃; for 3h;	75%

: 67-56-1
methanol

: 77-95-2
D-(-)-quinic acid

: 431-03-8
dimethylglyoxal

: 149-73-5
trimethyl orthoformate

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
With (1S)-10-camphorsulfonic acid for 24h; Reflux;	90%
With CSA	85%

...Expand

: 77-95-2
D-(-)-quinic acid

: 2695-47-8
6-Bromo-1-hexene

: 855252-32-3
(3R,5R)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid hex-5-enyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h;	88%

: 77-95-2
D-(-)-quinic acid

: 123-31-9
hydroquinone

Conditions

Conditions	Yield
With sodium hypochlorite; sulfuric acid for 10h; Heating;	87%

: 77-95-2
D-(-)-quinic acid

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Conditions

Conditions	Yield
	85%
With hydrogenchloride; acetone
With sulfuric acid; acetone

: 77-95-2
D-(-)-quinic acid

: 100-52-7
benzaldehyde

: 141171-64-4
(3aR,5R,7R,7aS)-5,7-Dihydroxy-2-phenyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	85%
With toluene-4-sulfonic acid In benzene Heating;	85%

: 67-56-1
methanol

: 77-95-2
D-(-)-quinic acid

: 431-03-8
dimethylglyoxal

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
With camphor-10-sulfonic acid; trimethyl orthoformate Heating;	85%
With camphor-10-sulfonic acid; trimethyl orthoformate Heating;	79%

...Expand

: 77-95-2
D-(-)-quinic acid

: 78-98-8
2-oxopropanal

: 149-73-5
trimethyl orthoformate

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
With (1S)-10-camphorsulfonic acid In methanol	85%

...Expand

: 211915-06-9
dabigatran etexilate

: 77-95-2
D-(-)-quinic acid

: 3-(((2-(((4-(N'-hexyloxicarbonylcarbamidoyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)piridin-2-ylamino)propionic acid ethyl ester D-(-)-quinate

Conditions

Conditions	Yield
In acetone at 20℃; for 4h;	84.7%

: 77-95-2
D-(-)-quinic acid

: 77-76-9
2,2-dimethoxy-propane

: 130474-38-3
3,4-isopropylidenequinide

Conditions

Conditions	Yield
Benzylsulfonic acid In benzene for 15h; Heating / reflux;	83.8%
With toluene-4-sulfonic acid In benzene for 18h; Heating;	18%
With toluene-4-sulfonic acid In acetone
In benzene Heating;

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.

Product Name

Quinic acid

Synthetic route

Quinic acid Specification

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