Basic information
- CAS
617-12-9- Standard SMILES
C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O)C(=O)O- InChIKey
WTFXTQVDAKGDEY-HTQZYQBOSA-N- Molecular formula
- C10H10O6
- Average molar mass
- 226.18 g/mol
- Monoisotopic mass
- 226.04773804
Overview
Chorismic acid is the (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid. It has a role as a Saccharomyces cerevisiae metabolite, a plant metabolite and an Escherichia coli metabolite. It is a conjugate acid of a chorismate(2-).
Names & identifiers
- Preferred name
- Chorismic Acid
- IUPAC
- (3R,4R)-3-(1-carboxyethenoxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
- English name
- Chorismic acid
- Molecular formula
- C10H10O6
- Molecular weight
- 226.18
Names & synonyms
chorismic acid617-12-9chorismateAcid, ChorismicGI1BLY82Y1(3R,4R)-3-(1-carboxyethenoxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acidCHEBI:17333DTXSID502106971,5-Cyclohexadiene-1-carboxylic acid, 3-((1-carboxyethenyl)oxy)-4-hydroxy-, (3R-trans)-(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid1,5-Cyclohexadiene-1-carboxylic acid, 3-[(1-carboxyethenyl)oxy]-4-hydroxy-, (3R-trans)-(3R,4R)-3-((1-carboxyeth-1-en-1-yl)oxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Show more names
chorismicaci(-)-ChorismateCHORISMIC ACID FREE ACID FROM &ChorisMic acid froM Enterobacter aerogenes >=80%2-[(3-Carboxy-6β-hydroxy-2,4-cyclohexadiene-1α-yl)oxy]acrylic acid(3R,4R)-3-((1-carboxyvinyl)oxy)-4-hydroxycyclohexa-1,5-dienecarboxylic acid
RefChem:388880DTXCID80133188Chorismic acid from Enterobacter aerogenes(3R,4R)-3-[(1-carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid1,5-Cyclohexadiene-1-carboxylic acid, 3-[(1-carboxyethenyl)oxy]-4-hydroxy-, (3R,4R)-1,5-Cyclohexadiene-1-carboxylic acid, 3-[(1-carboxyvinyl)oxy]-4-hydroxy-, (3R-trans)-(-)-Chorismic acid (3R-trans)-3-(1-Carboxyvinyloxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acidUNII-GI1BLY82Y1
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 392
Experimental & physicochemical properties
Melting Point140 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 105 · 105-108° (dec)
- alpha
- 21 · D21 -274° (c = 0.16 in water)
- Boiling point
- 556.1 · 556.1±50.0 °C(Predicted)
- Density
- 1.49 · 1.49±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- pka
- 3.59 · 3.59±0.11(Predicted)
- form
- powder
- InChI
- 1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1
- InChIKey
- WTFXTQVDAKGDEY-HTQZYQBOSA-N
- SMILES
- O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
- FDA UNII
- 1 BLY82Y1 · GI1BLY82Y1
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- risk_code
- 45-20/21/22-36/37/38-63
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-23-36/37/39-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H302+H312+H332-H315-H319-H335-H350-H361
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 1BEye Irrit. 2Repr. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313
Chemistry & industry
Applications
UsesChorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate derivatives.
Upstream & downstream products
Upstream raw materials
Suppliers20 total
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
Syntechem Co.,Ltd[email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
Related reactions
2 records
Compound notes
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