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Basic Information

Molecular Structure:
CAS No.:	138-59-0
Name:	Shikimic acid
Article Data:	38

Formula:	C₇H₁₀O₅
Molecular Weight:	174.153
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;
EINECS:	205-334-2
Density:	1.725 g/cm³
Melting Point:	185-187 ºC
Boiling Point:	400.5 ºC at 760 mmHg
Flash Point:	210.1 ºC
Solubility:	water: 18 g/100 mL (20 ºC)
Appearance:	white solid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	22-24/25-36-26
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

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Chemistry

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):

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.

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.

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.

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

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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