Shikimic acid

Base Information

• Chemical Name: Shikimic acid
• CAS No.: 138-59-0
• Molecular Formula: C7H10O5
• Molecular Weight: 174.153
• Hs Code.: 29181980
• European Community (EC) Number: 205-334-2
• UNII: 29MS2WI2NU
• DSSTox Substance ID: DTXSID4032039
• Nikkaji Number: J3.267K
• Wikipedia: Shikimic_acid
• Wikidata: Q410830
• Metabolomics Workbench ID: 38244
• ChEMBL ID: CHEMBL290345
• Mol file: 138-59-0.mol

Synonyms:Acid, Shikimic;Shikimic Acid

Chemical Property of Shikimic acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 4.45E-08mmHg at 25°C
• Melting Point: 185-187 ºC
• Refractive Index: -180 ° (C=1, H2O)
• Boiling Point: 400.5 ºC at 760 mmHg
• PKA: pK (14.1°) 5.19
• Flash Point: 210.1 ºC
• PSA: 97.99000
• Density: 1.725 g/cm³
• LogP: -1.51620
• Storage Temp.: -20°C Freezer
• Sensitive.: Hygroscopic
• Solubility.: 180g/l
• Water Solubility.: 18 g/100 mL (20 ºC)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 174.05282342
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

98% ^*data from raw suppliers

Shikimic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1C(C(C(C=C1C(=O)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O
• 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. Shikimic acid has been used as a standard for the quantification of shikimate in apical parts of roots. It has also been used as a substrate in shikimate kinase assay.

Technology Process of Shikimic acid

There total 104 articles about Shikimic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methyl shikimate (40983-58-2) → shikimic acid (138-59-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; for 5.5h; Ambient temperature;

DOI:10.1021/jo00385a022

Reference yield: 90.0%

(3R,4S,5R)-3,4-Diacetoxy-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (91758-39-3) → shikimic acid (138-59-0)

Guidance literature:

With sodium hydroxide; In methanol; at 5 - 25 ℃; for 2.5h;

Reference yield: 80.0%

(3aR,4S,7R,7aS)-methyl 4,7-dihydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate (1582806-01-6) → shikimic acid (138-59-0)

Guidance literature:

(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;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 10h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo402764v

upstream raw materials:

D-glucose

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

methyl shikimate

(-)-3-dehydroshikimic acid

Downstream raw materials:

methyl shikimate

benzoic acid

Refernces

• 1、 Fukuoka. "Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor". . p. 3219 - 3224. Retrieved 1982.
• 2、 Knop,Draths,Chandran,Barker,Von Daeniken,Weber,Frost. "Hydroaromatic equilibration during biosynthesis of shikimic acid". . p. 10173 - 10182. Retrieved 2001.
• 3、 Guo, Jiantao,Frost. "Synthesis of aminoshikimic acid". . p. 1585 - 1588. Retrieved 2004.
• 4、 Jiang, Shende,Mekki, Boualem,Singh, Gurdial,Wightman, Richard H.. "Enantiospecific synthesis of (-)-5-epi-shikimic acid and a new route to (-)-shikimic acid". . p. 5505 - 5508. Retrieved 1994.
• 5、 He, Yun-Gang,Huang, Yong-Kang,Xu, Zhang-Li,Xie, Wen-Jing,Luo, Yong-Qiang,Li, Feng-Lei,Zhu, Xing-Liang,Shi, Xiao-Xin. "Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules". . p. 4318 - 4332. Retrieved 2021/07/21.
• 6、 Morikawa, Toshio,Wang, Li-Bo,Ninomiya, Kiyofumi,Nakamura, Seikou,Matsuda, Hisashi,Muraoka, Osamu,Wu, Li-Jun,Yoshikawa, Masayuki. "Medicinal flowers. XXX. Eight new glycosides, everlastosides F - M, from the flowers of Helichrysum arenarium". experimental part. p. 853 - 859. Retrieved 2010/03/26.