Shikimic acid supplier | CasNO.138-59-0

Name
Shikimic acid
EINECS 205-334-2
CAS No. 138-59-0
Article Data38
CAS DataBase
Density 1.725 g/cm³
Solubility water: 18 g/100 mL (20 ºC)
Melting Point 185-187 ºC
Formula C₇H₁₀O₅
Boiling Point 400.5 ºC at 760 mmHg
Molecular Weight 174.153
Flash Point 210.1 ºC
Transport Information
Appearance white solid
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Bracken fern toxic component;3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid;L-Shikimic acid;3,4, 5-Trihydroxy-1-cyclohexene-1-carboxylic acid;(-)-Shikimic acid;3,4,5-trihydroxycyclohexene-1-carboxylic acid;1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))- (9CI);3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid;
PSA 97.99000
LogP -1.51620

Synthetic route

: 40983-58-2
methyl shikimate

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water for 5.5h; Ambient temperature;	97%
With sodium hydroxide In tetrahydrofuran; water	96%
With sodium hydroxide; water In tetrahydrofuran for 1h; Ambient temperature;	96%

: 91758-39-3
(3R,4S,5R)-3,4-Diacetoxy-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 5 - 25℃; for 2.5h;	90%
With sodium hydroxide 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h; Multistep reaction;

: 1582806-01-6
(3aR,4S,7R,7aS)-methyl 4,7-dihydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Stage #1: (3aR,4S,7R,7aS)-methyl 4,7-dihydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate With dmap; acetic anhydride; triethylamine In tetrahydrofuran for 3.66667h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 10h; Inert atmosphere; enantioselective reaction;	80%

: 1202183-69-4
(1S,2R,6R)-4-(ethoxycarbonyl)-6-(4-nitrobenzoyloxy)-cyclohex-3-ene-1,2-diyl diacetate

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With sodium hydroxide	65%

: C13H20O10

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 80℃; for 3h;	62%

: (3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-4,5-(2,3-dimethoxybutan-2,3-dioxy)cyclohex-1-ene-1-carboxylic acid

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In water	53%

: 40983-58-2
methyl shikimate

A: 138-59-0
shikimic acid

B: 171963-37-4
3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid

C: 99-96-7
4-hydroxy-benzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 100℃; for 30h;	A 8% B 21% C 21%

...Expand

: 2280-44-6
D-Glucose

Escherichia coli SP1.1/pJG6.181B: Escherichia coli SP1.1/pJG6.181B

A: 138-59-0
shikimic acid

B: 178948-66-8
5-deoxy-5-amino-shikimic acid

Conditions

Conditions	Yield
Stage #1: D-Glucose With Bacillus pumilus ATCC 21143; oxygen In various solvent(s) at 30℃; for 96h; Microbiological reaction; Stage #2: Escherichia coli SP1.1/pJG6.181B With oxygen In various solvent(s) at 37℃; Microbiological reaction;	A n/a B 5%

...Expand

: 50-99-7
D-glucose

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With cultures of escherichia coli; water at 35℃;

: 90927-40-5
3a,6,7,7a-tetrahydro-7-hydroxy-2,2-dimethyl-[3aR-(3aα,7α,7aα)]-1,3-benzodioxole-5-carboxylic acid

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With water; trifluoroacetic acid Ambient temperature; Yield given;
With trifluoroacetic acid for 10h; Ambient temperature; Yield given;
Multi-step reaction with 3 steps 1: CDCl3; pyridine / 48 h / Ambient temperature 2: aq. acetic acid / 2 h / 100 °C 3: aq. HCl / reflux 30 min, room temp. overnight View Scheme

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

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With NADPH at 20℃; Escherichia coli shikimate dehydrogenase, aq. phosphate buffer;
With Escherichia coli shikimate dehydrogenase; NADPH at 20℃; Kinetics; in aq. phosphate buffer;
With shikimate dehydrogenase
With NADP; ethylenediaminetetraacetic acid; D-glucose In phosphate buffer at 25℃; for 1.25h; pH=7;

: 95719-51-0
(-)-shikimic acid 3-O-gallate

A: 149-91-7
3,4,5-trihydroxybenzoic acid

B: 138-59-0
shikimic acid

Conditions

Conditions	Yield
tannase In water at 37℃; for 3h; Product distribution;	A 40 mg B 43 mg

: 87509-96-4
Acetic acid (1R,4R,6S)-4-acetoxy-6-((S)-2-hydroxy-3,3-dimethyl-butyryl)-cyclohex-2-enyl ester

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multistep reaction;

: 92592-01-3
(-)-t-butyl 3,4-O-isopropylideneshikimate

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With trifluoroacetic acid for 12h; Ambient temperature; Yield given;

: 73263-62-4
5-trans-caffeoylshikimic acid

A: 331-39-5
caffeic acid

B: 138-59-0
shikimic acid

Conditions

Conditions	Yield
In hydrogenchloride reflux 30 min, room temp. overnight;

: 95753-51-8
(-)-shikimic acid 3,4-O-digallate

A: 149-91-7
3,4,5-trihydroxybenzoic acid

B: 138-59-0
shikimic acid

Conditions

Conditions	Yield
tannase In water at 37℃; for 3h; Product distribution;	A 28 mg B 11 mg

: 95753-52-9
3,5-Di-O-galloylshikimic acid

A: 149-91-7
3,4,5-trihydroxybenzoic acid

B: 138-59-0
shikimic acid

Conditions

Conditions	Yield
tannase In water at 37℃; for 3h; Product distribution;	A 78 mg B 37 mg

: 74-90-8
hydrogen cyanide

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

: 138-59-0
shikimic 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

: 245054-34-6
methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran Hydrolysis;

: 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

: 625091-49-8
(3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid

A: 138-08-9
phosphoenolpyruvic acid

B: 138-59-0
shikimic acid

C: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

D: (3aR,7R,7aS)-2-Methyl-7-phosphonooxy-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-2,5-dicarboxylic acid

Conditions

Conditions	Yield
With glycine at 25℃; pH=2.5 - 3.5; Product distribution; Kinetics; Further Variations:; pH-values; Reagents;

...Expand

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

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Gluconobacter oxydans IFO 3244 cells / various solvent(s) / 20 h / 30 °C / pH 7 2: NADP; SKDH; GDH / D-glucose; EDTA / aq. phosphate buffer / 1.25 h / 25 °C / pH 7 View Scheme

: C13H16O4

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 59 percent / NaOH; BuNCl / toluene / 0.83 h / 5 °C 2: 52 percent / diphenyl ether / 1 h / 300 °C 3: 94 percent / BF3*OEt2 / toluene / 20 °C 4: KOH / tetrahydrofuran View Scheme

: 275355-06-1
(1R,5R,6R)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / BF3*OEt2 / toluene / 20 °C 2: KOH / tetrahydrofuran View Scheme

: C13H14O4

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: NaBH4; NaOH / methanol; H2O / 0 °C 2: 59 percent / NaOH; BuNCl / toluene / 0.83 h / 5 °C 3: 52 percent / diphenyl ether / 1 h / 300 °C 4: 94 percent / BF3*OEt2 / toluene / 20 °C 5: KOH / tetrahydrofuran View Scheme

: C13H15O4C7H5O

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 52 percent / diphenyl ether / 1 h / 300 °C 2: 94 percent / BF3*OEt2 / toluene / 20 °C 3: KOH / tetrahydrofuran View Scheme

: 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

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 12 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: DBU, MeOH / 20 h / -20 °C 9: 23 h / Ambient temperature 10: Tf2O, (i-Pr)2NEt / toluene / 1 h / 50 °C 11: 95 percent / HCl / methanol / 40 h / Ambient temperature 12: 96 percent / NaOH, H2O / tetrahydrofuran / 1 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 12 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: DBU, MeOH / 20 h / -20 °C
9: 23 h / Ambient temperature
10: Tf2O, (i-Pr)2NEt / toluene / 1 h / 50 °C
11: 95 percent / HCl / methanol / 40 h / Ambient temperature
12: 96 percent / NaOH, H2O / tetrahydrofuran / 1 h / Ambient temperature
View Scheme

: 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

: 138-59-0
shikimic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 94 percent / imidazole / CH2Cl2 2: 97 percent / DIBAL / tetrahydrofuran / 0 °C 3: 92 percent / n-Bu3P / tetrahydrofuran / Ambient temperature 4: 1.) m-chloroperoxybenzoic acid; 2.) TFAA, 2,6-lutidine / 1.) CH2Cl2, 0 deg C; 2.) CH2Cl2 5: 59 percent / NaClO2, Na2PO4, 2-methyl-2-butene / H2O; 2-methyl-propan-2-ol 6: 53 percent / TFA / H2O View Scheme

methanol: methanol

: 138-59-0
shikimic acid

: 40983-58-2
methyl shikimate

Conditions

Conditions	Yield
With Amberlite IR 120 for 16h; Heating;	100%
With Amberlite-IR120 at 65℃; for 18h; Esterification;	100%
With hydrogenchloride at 60℃; for 6h;	100%

: 186581-53-3, 908094-01-9
diazomethane

: 138-59-0
shikimic acid

: 40983-58-2
methyl shikimate

Conditions

Conditions	Yield
In methanol; diethyl ether for 15h; Ambient temperature;	99%
In methanol
In methanol; diethyl ether at -20 - -15℃;

: 138-59-0
shikimic acid

: 431-03-8
dimethylglyoxal

: 149-73-5
trimethyl orthoformate

: 245054-32-4
methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Conditions

Conditions	Yield
With sulfuric acid In methanol for 48h; Inert atmosphere; Reflux;	95%
With 10-camphorsufonic acid In methanol at 85℃; Condensation;	80%
With CSA In methanol for 48h; Inert atmosphere; Reflux;	70%
With (1S)-10-camphorsulfonic acid In methanol for 72h; Reflux; Inert atmosphere;	62%

...Expand

: 64-17-5
ethanol

: 138-59-0
shikimic acid

: 101769-63-5
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With KU-2-8 cationite for 15h; Reflux;	93%
With thionyl chloride at 140℃; under 7500.75 Torr; for 0.133333h; Reagent/catalyst; Temperature; Time;	93%
With thionyl chloride for 3h; Reflux;	83%

: 67-56-1
methanol

: 138-59-0
shikimic acid

: 108-94-1
cyclohexanone

: 120200-03-5
methyl (3aS,4R,7aR)-4-hydroxy-3a,4,5,7a-tetrahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-6-carboxylate

Conditions

Conditions	Yield
With (1S)-10-camphorsulfonic acid In toluene at 160℃; for 0.5h; Microwave irradiation;	92%
With camphor-10-sulfonic acid In toluene at 160℃; Microwave irradiation;

...Expand

: 138-59-0
shikimic acid

trans-p-coumaroyl-COA: trans-p-coumaroyl-COA

: 5-O-(p-coumaroyl)shikimic acid

Conditions

Conditions	Yield
In water at 35℃; for 6h; dark; shikimate-p-hydroxycinnamoyl transferase;	68%

: 108-22-5
Isopropenyl acetate

: 138-59-0
shikimic acid

: 98167-08-9
(3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid

Conditions

Conditions	Yield
With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique;	66%

: 138-59-0
shikimic acid

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

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 65℃;	60%
With NAD(P)-independent quinate dehydrogenase EC 1.1.99.25; potassium hexacyanoferrate(III) Enzyme kinetics; Further Variations:; Reagents;
With oxygen In water at 20℃; under 760.051 Torr; for 336h; pH=6.5 - 7;

: 138-59-0
shikimic acid

A: 99-06-9
3-Carboxyphenol

B: 99-96-7
4-hydroxy-benzoic acid

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 120℃; for 16h;	A 9% B 57%
With hydrogenchloride for 14h; Heating;	A 13% B 40%

: 138-59-0
shikimic acid

A: 99-06-9
3-Carboxyphenol

B: 108-95-2
phenol

C: 99-96-7
4-hydroxy-benzoic acid

Conditions

Conditions	Yield
Stage #1: shikimic acid In water at 350℃; for 0.5h; Stage #2: With copper In water at 350℃;	A 18 % Chromat. B 51% C 1 % Chromat.

...Expand

: 138-59-0
shikimic acid

: 93060-75-4, 143393-03-7
(-)-shikimate 3-phosphate trisodium salt

Conditions

Conditions	Yield
With ATP shikimate kinase, 1.) 6 h, 2.) 13 deg C., overnight;	47%
Multi-step reaction with 11 steps 1: 95 percent / Amberlite IR 120 / 12 h / Heating 2: 96 percent / camphorsulfonic acid / 0.25 h / Ambient temperature 3: 100 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature 4: 94 percent / aq. HOAc / tetrahydrofuran / 6 h / 70 °C 5: 1.) dibutyltin oxide / 1.) benzene, reflux, 1 h, 2.) DMF, 30 min 6: 100 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 1 h / 50 °C 7: 89 percent / 80percent aq. HOAc / 0.25 h 8: tetrazole / CH2Cl2 / 2 h / Ambient temperature 9: 0.304 g / m-CPBA / CH2Cl2 / 2 h / -40 °C 10: 80 percent / bromotrimethylsilane / CH2Cl2 / 1 h / 0 °C 11: 99 percent / 1 N NaOH / 3 h / 0 °C View Scheme

Yield

With ATP shikimate kinase, 1.) 6 h, 2.) 13 deg C., overnight;

47%

Multi-step reaction with 11 steps
1: 95 percent / Amberlite IR 120 / 12 h / Heating
2: 96 percent / camphorsulfonic acid / 0.25 h / Ambient temperature
3: 100 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
4: 94 percent / aq. HOAc / tetrahydrofuran / 6 h / 70 °C
5: 1.) dibutyltin oxide / 1.) benzene, reflux, 1 h, 2.) DMF, 30 min
6: 100 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 1 h / 50 °C
7: 89 percent / 80percent aq. HOAc / 0.25 h
8: tetrazole / CH2Cl2 / 2 h / Ambient temperature
9: 0.304 g / m-CPBA / CH2Cl2 / 2 h / -40 °C
10: 80 percent / bromotrimethylsilane / CH2Cl2 / 1 h / 0 °C
11: 99 percent / 1 N NaOH / 3 h / 0 °C
View Scheme

: 138-59-0
shikimic acid

: 79074-45-6
2-(bromomethyl)-3,5,6-trimethylpyrazine

: 1396810-49-3
(3,5,6-trimethyl pyrazine-2-yl)methyl 3,4,5-trihydroxycyclohexyl-1-ene formate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 3.5h; Reflux;	43.8%

: 138-59-0
shikimic acid

H-Lys-Cys(StBu)-Gly-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin: H-Lys-Cys(StBu)-Gly-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin

: C29H47N5O11S2

Conditions

Conditions	Yield
Stage #1: shikimic acid; H-Lys-Cys(StBu)-Gly-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: With chlorotriisopropylsilane; trifluoroacetic acid In water at 20℃; for 1h;	40%

: 138-59-0
shikimic acid

: N-aminoethyl-N,N-di-n-tetradecylamine

: 1000022-16-1
C37H72N2O4

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;	33%

: 138-59-0
shikimic acid

H-Lys-Cys(StBu)-Arg(Pmc)-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin: H-Lys-Cys(StBu)-Arg(Pmc)-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin

: C33H56N8O11S2

Conditions

Conditions	Yield
Stage #1: shikimic acid; H-Lys-Cys(StBu)-Arg(Pmc)-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: With chlorotriisopropylsilane; trifluoroacetic acid In water at 20℃; for 1h;	26%

: 138-59-0
shikimic acid

: 67436-13-9
(R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

: 75932-02-4, 78081-87-5
N-2,N-6-bis(9-fluorenylmethyloxycarbonyl)-L-lysine

Fmoc-Gly-O-Wang ester resin: Fmoc-Gly-O-Wang ester resin

: Nα,Nε-Bis-[(3R,4S,5R)-3,4,5-trihydroxycyclohexanecarbonyl]-L-lysyl-[S-(tert-butylthio)]-L-cysteinyl-glycine

Conditions

Conditions	Yield
Multistep reaction;	14%

...Expand

Shikimic acid Chemical Properties

IUPAC name: (3R,4S,5R)-3,4,5-Trihydroxycyclohexene-1-carboxylic acid
Molecular Formula: C₇H₁₀O₅
Molecular Weight: 174.15 g/mol
EINECS: 205-334-2
Melting point: 185-191 °C
alpha: -180 º (c=4, H2O 25 °C)
Water solubility: 18 g/100 mL (20 °C)
Index of Refraction: 1.679
Sensitive: Hygroscopic
Merck: 14,8480
Density: 1.725 g/cm³
Flash Point: 210.1 °C
Surface Tension: 116.6 dyne/cm
Enthalpy of Vaporization: 75.28 kJ/mol
Boiling Point: 400.5 °C at 760 mmHg
Vapour Pressure: 4.45E-08 mmHg at 25 °C
Product Category of Shikimic acid (CAS NO.138-59-0): API intermediates;Chiral Reagents;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Natural Plant Extract
Following is the structure of Shikimic acid (CAS NO.138-59-0):

Shikimic acid Uses

Naturally, Shikimic acid (CAS NO.138-59-0) occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, flavonpids and other important aromatic substance.

Shikimic acid Toxicity Data With Reference

1.	dlt-mus-ipr 1000 mg/kg	BJLSAF Botanical Journal of the Linnean Society. 73 (1976),105.
2.	dlt-mus-orl 3200 mg/kg	NATUAS Nature. 250 (1974),348.
3.	otr-ham:kdy 250 mg/L	TOLED5 Toxicology Letters. 19 (1983),43.
4.	ipr-mus LD50:1000 mg/kg	NATUAS Nature. 250 (1974),348.

Shikimic acid (CAS NO.138-59-0) has been listed as a carcinogen by IARC in Group 3. The toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Shikimic acid Consensus Reports

IARC Cancer Review: Group 3 IMEMDT . IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 40 ,1986,p. 47.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Shikimic acid Safety Profile

Shikimic acid's safety information: Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition, it emits acrid smoke and irritating fumes.
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R37/38:Irritating to respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: GW4600000
F: 3-10
HS Code: 29181980

Shikimic acid Specification

Shikimic acid , with a CAS number of 138-59-0, known as 3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid ; and 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid . And its classification code are mutation data, natural product, tumor data. Shikimic acid (CAS NO.138-59-0) could be stable under normal temperatures and pressures. And it should avoid the condition like strong oxidants. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, irritating and toxic fumes and gases, carbon dioxide. Its hazardous polymerization has not been reported.

Product Name

Shikimic acid

Synthetic route

Shikimic acid Chemical Properties

Shikimic acid Uses

Shikimic acid Toxicity Data With Reference

Shikimic acid Consensus Reports

Shikimic acid Safety Profile

Shikimic acid Specification

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