(3R,4R)-3-[(1-カルボキシエテニル)オキシ]-4-ヒドロキシ-1,5-シクロヘキサジエン-1-カルボン酸

Chorismic Acid

HCID 12039CAS 617-12-9

基本情報

標準SMILES: C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O)C(=O)O
InChIKey: WTFXTQVDAKGDEY-HTQZYQBOSA-N
分子式: C10H10O6
平均分子量: 226.18 g/mol
単同位体質量: 226.04773804

概要

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-).

名称と識別子

優先名称: Chorismic Acid
IUPAC: (3R,4R)-3-(1-carboxyethenoxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
現地名: (3R,4R)-3-[(1-カルボキシエテニル)オキシ]-4-ヒドロキシ-1,5-シクロヘキサジエン-1-カルボン酸
英語名: Chorismic acid
分子式: C10H10O6
分子量: 226.18

名称と別名

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

名称をさらに表示

コリスマート(-)-コリスム酸(3R,4R)-3-[(1-カルボキシエテニル)オキシ]-4-ヒドロキシ-1,5-シクロヘキサジエン-1-カルボン酸コリスミン酸(-)-コリスミン酸2-[(3-カルボキシ-6β-ヒドロキシ-2,4-シクロヘキサジエン-1α-イル)オキシ]アクリル酸コリスミ酸(3R)-3β-(1-カルボキシエテニルオキシ)-4α-ヒドロキシ-1,5-シクロヘキサジエン-1-カルボン酸コリスミン酸 ENTEROBACTER AEROGENES由来(3R,4R)-3-[(1-カルボキシエタ-1-エン-1-イル)オキシ]-4-ヒドロキシシクロヘキサ-1,5-ジエン-1-カルボン酸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

データベース識別子

CAS: 617-12-9
PubChem CID: 12039
DTXSID: DTXSID50210697
ChEBI: CHEBI:17333
UNII: GI1BLY82Y1
EC Number: 636-403-9
Nikkaji: J7.035A

物性

構造計算による物性

XLogP: 0.2
極性表面積: 104 Å²
水素結合供与体数: 3
水素結合受容体数: 6
回転可能結合数: 4
重原子数: 16
形式電荷: 0
複雑度: 392

実験および物理化学的性質

Melting Point140 °C

Physical DescriptionSolid

物理化学的性質

融点: 105 · 105-108° (dec)
比旋光度: 21 · D21 -274° (c = 0.16 in water)
沸点: 556.1 · 556.1±50.0 °C(Predicted)
比重(密度): 1.49 · 1.49±0.1 g/cm3(Predicted)
貯蔵温度: -20 °C · -20°C
酸解離定数(Pka): 3.59 · 3.59±0.11(Predicted)
外見: 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

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk: 3
risk_code: 45-20/21/22-36/37/38-63
hazard_code: T
safety_code: 53-23-36/37/39-45
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 1BEye Irrit. 2Repr. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

応用分野

使用Chorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate derivatives.

上流・下流製品情報

上流原料

5-enol-pyruvoylshikimate 3-phosphate (EPSP)(-)-シキミ酸メチル 2-(ホスホノオキシ)プロペン酸/カリウム,(1:1)シキミ酸

サプライヤー20 社

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]

補足説明

定義ChEBI: The (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid.