Shikimic acid

Iupac Name：(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid

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+

Request For Quotation

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:?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?

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.

View all

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

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

138-59-0Total: 69 Synthesis Route

50-99-7 475 Suppliers

138-59-0 373 Suppliers

Literatures:
Journal of Biological Chemistry, , vol. 220, p. 477,493
Yield: null

77-95-2 78 Suppliers

138-59-0 373 Suppliers

Literatures:
Bioscience, Biotechnology and Biochemistry, , vol. 70, # 10 p. 2579 - 2582
Yield: null

2922-42-1 13 Suppliers

138-59-0 373 Suppliers

Literatures:
Tetrahedron Letters, , vol. 29, # 51 p. 6779 - 6782
Yield: null

View all

8. Precursor and Product

precursor:

92592-01-3

40983-58-2

88400-38-8

76985-85-8

76985-84-7

91758-39-3

77-95-2

88400-34-4

88400-36-6

2280-44-6

88400-41-3

23330-72-5

88165-22-4

88400-33-3

87509-96-4

2922-42-1

92591-97-4

88400-32-2

88165-26-8

88424-81-1

50-99-7

90927-40-5

88165-24-6

View all

product :

19438-10-9

204255-11-8

63959-45-5

2922-42-1

204255-06-1

271-44-3

77-95-2

582-33-2

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==

11. Recommended Suppliers

Global369SuppliersView all >>

Hebei Ruiyao Biotechnology Co., Ltd Diamond member

2YRS

Products:Cosmetic Grade Chemical Raw Materical,Chemicals Raw Materials,API,Pharmaceutical Intermediates,Organic Chemicals
Tel:0311-88180881-19932768658
Email:sale02@ruiyaobio.com

Natural Organic CAS 138-59-0 Lllicium Verum Powder

Purity:99%Packing: 200kg/bag FOB
Price: 50 USD/kg
Time: 2023/05/30

Inquire

Hebei Zebo Biotechnology Co., LTD Diamond member

2YRS

Products:Organic intermediates, Organic solvents,Cosmetic raw materials ...
Tel:00-86-18034554576
Email:Ella@hbzebo.com

Shikimic acid cas 138-59-0

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kg
Time: 2023/05/30

Inquire

Hebei Crovell Biotech Co. Ltd Diamond member

3YRS

Products:Cosmetic Raw Materials,solvents,etc.
Tel:86-311-66562153
Email:breeduan@crovellbio.com

Factory supply Shikimic acid Cas 138-59-0 from China

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kilogram
Time: 2023/05/30

Inquire

Wuhan Xiju Biotechnology Co., Ltd. Diamond member

2YRS

Products:My whatsapp:+86 13043111536 cas no.1451-82-7,79099-07-3,5449-12-7,5337-93-9,49851-31-2,288573-56-8
Tel:86-311-13294182928
Email:April@wh-xiju.com

Test Sample Is Free----Shikimic Acid CAS 138-59-0

Purity:99%Packing: 200kg/bag FOB
Price: 6 USD/kg
Time: 2023/05/30

Inquire

Wuhan Pharmchem Co., LTD. Diamond member

2YRS

Products:Pharma &Food Intermediates Water Treatment Chemicals Industrial Specialties Fine Chemicals
Tel:86-27-85835203
Email:steven@cspharmchem.com

Shikimic acid 98% Illicium verum extract EINECS 205-334-2

Purity:99%Packing: 200kg/bag FOB
Price: 125 USD/kg
Time: 2023/05/30

Inquire

12. Realated Product Infomation

21967-35-1 (-)-4-epi-Shikimic acid

101769-63-5 ShikiMic Acid Ethyl Ester

183075-03-8 3,4-O-Isopropylidene shikimic acid

63959-45-5 SHIKIMATE-3-PHOSPHATE

71010-76-9 Decanoic acid, mixed esters with heptanoic acid, octanoic acid, pentaerythritol and valeric acid

68130-51-8 Decanoic acid, mixed esters with heptanoic acid, isovaleric acid, octanoic acid and pentaerythritol

68130-55-2 Hexanedioic acid, mixed esters with decanoic acid, heptanoic acid, octanoic acid and pentaerythritol

Recently Updated : 154323-59-8 147405-49-0 147405-54-7 147405-42-3 147405-52-5 2551114-72-6 156937-00-7 1824482-48-5 1378828-01-3 1849331-98-1