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Shikimic acid

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Name

Shikimic acid

EINECS 205-334-2
CAS No. 138-59-0 Density 1.725 g/cm3
PSA 97.99000 LogP -1.51620
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 N/A Appearance white solid
Safety 22-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 138-59-0 (Shikimic acid) Hazard Symbols IrritantXi
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;

Article Data 38

Shikimic acid Synthetic route

40983-58-2

methyl shikimate

138-59-0

shikimic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 5.5h; Ambient temperature;97%
With sodium hydroxide In tetrahydrofuran; water96%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium hydroxide65%

C13H20O10

138-59-0

shikimic acid

Conditions
ConditionsYield
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
ConditionsYield
With trifluoroacetic acid In water53%
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
ConditionsYield
With hydrogenchloride; water at 100℃; for 30h;A 8%
B 21%
C 21%
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
ConditionsYield
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%
50-99-7

D-glucose

138-59-0

shikimic acid

Conditions
ConditionsYield
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
ConditionsYield
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

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: IrritantXi
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.

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