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(-)-Shikimic acid - for synthesis, high purity , CAS No.138-59-0
Basic Description
Synonyms
SPECTRUM1502256 | Spectrum5_000386 | 2aa9 | 3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid | SR-01000632403-5 | KBio2_006848 | MEGxp0_001939 | B1A53F8A-8664-405D-8370-A9785ADD2D0B | bmse000114 | EC 205-334-2 | Shicimic Acid | Shikimic acid, >=99% | VEROCHI
Specifications & Purity
for synthesis
Storage Temp
Room temperature
Shipped In
Normal
Grade
for synthesis
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Organic oxygen compounds
Class
Organooxygen compounds
Subclass
Alcohols and polyols
Intermediate Tree Nodes
Cyclic alcohols and derivatives - Cyclitols and derivatives
Direct Parent
Shikimic acids and derivatves
Alternative Parents
Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework
Aliphatic homomonocyclic compounds
Substituents
Shikimic acid or derivatives - Secondary alcohol - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic homomonocyclic compound
Description
This compound belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.
External Descriptors
alpha,beta-unsaturated monocarboxylic acid - cyclohexenecarboxylic acid - hydroxy monocarboxylic acid
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
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
InChIKey
JXOHGGNKMLTUBP-HSUXUTPPSA-N
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
WGK Germany
3
RTECS
GW4600000
PubChem CID
8742
Molecular Weight
174.15
Beilstein
2210055
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Specific Rotation[α]
-180 ° (C=1, H2O)
Melt Point(°C)
185-187°C
Molecular Weight
174.150 g/mol
XLogP3
-1.700
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Exact Mass
174.053 Da
Monoisotopic Mass
174.053 Da
Topological Polar Surface Area
98.000 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
222.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
3
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Yao Zhu, Xingqi Shao, Ziyu Yuan, Jian Rong, Tao Zhang, Dongya Yang, Jianming Pan, Fengxian Qiu.
(2024)
Construction of Sustainable Biomass Bubble Propulsion Micromotor and Selective Recognition/Separation of Shikimic Acid with Open 3D Target Imprinting Cavity. ACS Sustainable Chemistry & Engineering,
12
(2):
(1104–1115).
2.
Faguang Ma, Ming Yan, Rongxin Lin, Yilin Wu, Jianming Pan.
(2024)
Boronate-affinity sol–gel-imprinted membranes with MOFs-functionalized rotary-evaporating layers for high-precision specific recognition. SEPARATION AND PURIFICATION TECHNOLOGY,
330
(125458).
3.
Yilin Wu, Faguang Ma, Jingjing Zhen, Jianming Pan.
(2024)
Nanofluid-based wooden imprinted membranes with precise-designed nanocages for ultrafast and super-sensitive recognition and separation. SEPARATION AND PURIFICATION TECHNOLOGY,
328
(125038).
4.
Ensheng Zhang, Long Jiang, He Li, Shuping Wang, Guixue Zhang, Anzhang Li, Weiheng Kong, Yan Zhao, Meihao Xiang, Ping Ju, Fengli Qu.
(2023)
The inter-molecular hydrogen bonds modulated reversible ACQ-AIE conversion and dual-states sensing applications of shikimic acid derived hydrogen bond dimers. DYES AND PIGMENTS,
219
(111616).
5.
Ran Xin, Meng Dong, Yu-Ying Zhang, Xu-Hui Huang, Xiu-Ping Dong, Lei Qin.
(2023)
Development and validation of a HILIC-MS/MS method for simultaneous quantitative of taste-active compounds in foods. JOURNAL OF FOOD COMPOSITION AND ANALYSIS,
120
(105302).
6.
Kaicheng Zhang, Yue Li, Zequan Diao, Hang Cui, Faguang Ma, Ming Yan, Yilin Wu.
(2023)
Precise identification and transport of specific molecules through framework-functionalized membranes with multiple binding sites. JOURNAL OF MEMBRANE SCIENCE,
670
(121327).
7.
Li Qiaofeng, Lan Taijin, He Songhua, Chen Weiwei, Li Xiaolan, Zhang Weiquan, Liu Ying, Zhang Qiuping, Chen Xin, Han Yaoyao, Su Zhiheng, Zhu Dan, Guo Hongwei.
(2021)
A network pharmacology-based approach to explore the active ingredients and molecular mechanism of Lei-gong-gen formula granule on a spontaneously hypertensive rat model. Chinese Medicine,
16
(1):
(1-21).
8.
Yao Zhu, Ziyu Yuan, Jian Rong, Tao Zhang, Dongya Yang, Jianming Pan, Fengxian Qiu.
(2024)
Engineering flower-shaped hierarchical micromotors on a sustainable biotemplate by teamed boronate affinity-based surface imprinting for effective separation of shikimic acid. SEPARATION AND PURIFICATION TECHNOLOGY,
336
(126345).
9.
Jiale Hu, Zhigang Wang, Weihui Xu.
(2024)
Production-optimized fermentation of antifungal compounds by Bacillus velezensis LZN01 and transcriptome analysis. Microbial Biotechnology,
17
(10):
(e70026).
10.
Tai Wen, Junyao Li, Wenrong Cai, Datong Wu, Zheng-Zhi Yin, Yong Kong.
(2024)
Visual and electrochemical chiral discrimination of tryptophan isomers with shikimic acid chiral ionic liquids–copper ions complex. TALANTA,
272
(125850).
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10 Citations