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Home> Encyclopedia >Forest chemicals>Pharmaceutical Intermediates>Organic Intermediate
Shikimic acid structure
Shikimic acid structure

Shikimic acid

Iupac Name:(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
CAS No.: 138-59-0
Molecular Weight:174.1513
Modify Date.: 2022-11-12 07:05
Introduction: Naturally 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 compounds. View more+
1. Names and Identifiers
1.1 Name
Shikimic acid
1.2 Synonyms

(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (-)-Shikimic acid (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (3R,4S,5R)-3,4,5-TRIHYDROXY-1-CYCLOHEXENECARBOXYLIC ACID (3R,4S,5R)-3,4,5-TRIHYDROXY-CYCLOHEX-1-ENECARBOXYLIC ACID [3R-(3α,4α,5β)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, [3R-(3α,4α,5β)]- 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid 3,4,5-Trihydroxycyclohex-1-enecarboxylic acid Illicium Verum P.E. L-SHIKIMIC ACID NSC 59257 Shikimic acid methyl esther Shikimic acid,(3R,4S,5R)-()-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid

1.3 CAS No.
138-59-0
1.4 CID
8742
1.5 EINECS(EC#)
205-334-2
1.6 Molecular Formula
C7H10O5 (isomer)
1.7 Inchi
InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
1.8 InChkey
JXOHGGNKMLTUBP-HSUXUTPPSA-N
1.9 Canonical Smiles
C1C(C(C(C=C1C(=O)O)O)O)O
1.10 Isomers Smiles
C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O
2. Properties
2.1 Density
1.725
2.1 Melting point
185-191℃
2.1 Boiling point
400.5 oC at 760 mmHg
2.1 Refractive index
-180 ° (C=1, H2O)
2.1 Flash Point
210.1 oC
2.1 Precise Quality
174.05300
2.1 PSA
97.99000
2.1 logP
-1.51620
2.1 Solubility
180g/l
2.2 Appearance
white powder
2.3 Storage
Hygroscopic. Ambient temperatures.
2.4 Chemical Properties
White Solid
2.5 Color/Form
Powder
2.6 Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.
2.7 pKa
pK (14.1°) 5.19
2.8 Water Solubility
18 g/100 mL (20 oC)
2.9 Spectral Properties
IR: 2:277F (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
UV max (alcohol): 213 nm (E = 8900)
2.10 Stability
Stable under normal temperatures and pressures.
2.11 StorageTemp
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
3. Use and Manufacturing
3.1 Definition
ChEBI: A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microrganisms. Shikimic acidSupplier
3.2 Usage
Naturally 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 compounds.
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S24/25
4.1 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
4.2 RIDADR
REM
4.2 WGK Germany
3
4.2 RTECS
GW4600000
4.2 Report

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.

4.3 Safety

?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?

4.4 Sensitive
Hygroscopic
4.5 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.

4.6 Toxicity
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.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
Antagonistic antimicrobial agent which also inhibits rapamycin biosynthesis
9.1 Merck
14,8480
9.2 BRN
4782717
9.3 Chemical Properties
White Solid
9.4 Uses
Naturally 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 compounds.
9.5 Definition
ChEBI: A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and micro rganisms.
10. Computational chemical data
  • Molecular Weight: 174.1513g/mol
  • Molecular Formula: C7H10O5
  • Compound Is Canonicalized: True
  • XLogP3-AA: -1.7
  • Exact Mass: 174.05282342
  • Monoisotopic Mass: 174.05282342
  • Complexity: 222
  • Rotatable Bond Count: 1
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 5
  • Topological Polar Surface Area: 98
  • Heavy Atom Count: 12
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBgOAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAGgAACAAADBSggAIACAAAAgCIAiDSCAAAAAAgAAAACAEAAEgBFBIAAQAAUAAFwAAJEYPK7CTAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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