ゲンチシン酸

2,5-Dihydroxybenzoic acid

HCID 3469CAS 490-79-9
部分構造検索類似構造を探す

基本情報

標準SMILES
O=C(O)c1cc(O)ccc1O
InChIKey
WXTMDXOMEHJXQO-UHFFFAOYSA-N
分子式
C7H6O4
平均分子量
154.12 g/mol
単同位体質量
154.02660867

名称と識別子

優先名称
2,5-Dihydroxybenzoic acid
IUPAC
2,5-dihydroxybenzoic acid
現地名
ゲンチシン酸
英語名
2,5-Dihydroxybenzoic acid
分子式
C7H6O4
分子量
154.12

名称と別名

2,5-DIHYDROXYBENZOIC ACIDgentisic acid490-79-9Benzoic acid, 2,5-dihydroxy-5-Hydroxysalicylic acidHydroquinonecarboxylic acidGensigenGensigon2,5-Dhba2,5-Dioxybenzoic acidSalicylic acid, 5-hydroxy-Kyselina gentisinova
名称をさらに表示
2,5-ジヒドロキシ安息香酸3,6-ジヒドロキシ安息香酸ゲンチジン酸ゲンシゴンカルボキシヒドロキノン5-ヒドロキシサリチル酸ゲンシゲン2,5‐ジヒドロキシ安息香酸2,5-ジヒドロキシ安息香酸 (DHB)2,5-ジヒドロキシ安息香酸, 99%ゲンチシン酸DHBGentisateGentisicPhloretate2,5-dihydroxybenzoic2,5-Dihydroxybenzoes?ureKyselina 2,5-dihydroxybenzoova
Acido gentisicoAcide gentisiqueAcidum gentisicumVP36V95O3TNSC-27224DTXSID4060078CHEBI:17189RefChem:639843

データベース識別子

CAS
490-79-9
PubChem CID
3469
DTXSID
DTXSID4060078
ChEMBL
CHEMBL1461
ChEBI
CHEBI:17189
UNII
VP36V95O3T
EC Number
207-718-5
Nikkaji
J6.046A

物性

構造計算による物性

XLogP
1.6
極性表面積
77.8 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
1
重原子数
11

実験および物理化学的性質

LogP1.74
Solubility5.0 mg/mL at 5 °C
Melting Point199.5 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description · 2 件

Solid; [Merck Index] Light yellow crystals; [Aldrich MSDS]

Solid

Collision Cross Section · 2 件

122.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

125 Ų [M-H]-

物理化学的性質

融点
204 · 204-208 °C(lit.)
沸点
237.46 °C · 237.46°C (rough estimate)
比重(密度)
1.3725 · 1.3725 (rough estimate)
屈折率
1.64 · 1.6400 (estimate)
貯蔵温度
30 °C · Store below +30°C.
溶解性
アルコール、エーテルに溶ける。
化学的性質 · 1 件

化学的特性White to light beige crystalline powder. 2,5-Dihydroxybenzoic Acid [490-79-9] (gentisic acid, 2,5-DHBA), C7H6O4, Mr 154.1, mp 205 C, is soluble in water and alcohols but insoluble in benzene and chloroform. The acid is stable in boiling water and gives a deep blue color with iron(III) chloride. Here, the acid decomposes to form p-benzoquinone [106-51-4] and carbon dioxide. 2–5-Dihydroxybenzoic acid is used as an antirheumatic drug and, more recently, as a color developer for thermal paper.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.

Warning

H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (94%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (94%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (92.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 67 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 67 reports by companies.；There are 10 notifications provided by 66 of 67 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 2 件

Chemical: Benzoic acid, 2,5-dihydroxy-

Benzoic acid, 2,5-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses convulsions in intravenous lethal-dose studies of mice; [RTECS] A skin and strong eye irritant; Harmful by ingestion and skin absorption; Evidence of reproductive toxicity in experimental animals; [Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (94%)；Skin Irrit. 2 (94%)；Eye Irrit. 2 (94%)；STOT SE 3 (92.5%)

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin

法規制情報

Regulatory Information · 2 件

Chemical: Benzoic acid, 2,5-dihydroxy-

Benzoic acid, 2,5-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard

安全データ

wgk
3
tsca
TSCA listed
rtecs
LY3850000
hs_code
29182990
risk_code
22-36/37/38
化審法
(3)-1616, (3)-3065

化学と産業

薬理情報

Metabolism/Metabolites5-hydroxylation is a known human metabolite of salicylic acid.
Cellular LocationsCytoplasm

用途と製造

Uses · 2 件

Excreted in urine of dogs following ingestion of salicylates; Used therapeutically (analgesic and anti-inflammatory); [Merck Index] An oxidative product of saligenin; [ChemIDplus] Used as an analgesic medicine; [Hawley]

Synthetic Polymer MALDI Matrix Compounds

Household ProductsInformation on 1 consumer products that contain Gentisic acid in the following categories is provided:；• Personal Care
General Manufacturing InformationBenzoic acid, 2,5-dihydroxy-: ACTIVE
応用分野 · 6 件

解説ゲンチシン酸,針状晶．融点205 ℃(200 ℃ で昇華)．水，エタノール，エーテルに可溶，ベンゼンに不溶．動物体内ではチロシンから生合成され，5-メトキシサリチル酸として排泄される．森北出版「化学辞典（第2版）

用途ペプチド、糖、糖脂質試料のマトリックス。

用途ヒドロキノンと同じように容易に酸化されるため、医薬品の抗酸化賦形剤として用いられる。 実験室では、マトリックス支援レーザー脱離イオン化法(MALDI)質量分析法のサンプルマトリックスに用いられる。

説明Gentisic acid is a dihydroxy benzoic acid. It is a derivative of benzoic acid and a minor (1 %) product of the metabolic break down of aspirin, excreted by the kidneys. It is also found in the African tree Alchornea cordifolia and in wine.

使用2,5-dihydroxybenzoic acid areused as intermediates for pharmaceuticals (especially for antipyetic anlgesic, antirheumatism) and other organic synthesis. They are used as matrix for ionization of peptides, proteins and carbohydrates. In industrial field, they areused as intermediates for the production of other organic chemicals, resins, polyesters, plasticizers, dyestuffs, preservatives, and rubber chemicals.

一般的な説明Aspirin metabolite.

調製方法

Gentisic acid is produced by carboxylation of hydroquinone. C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2 This conversion is an example of a Kolbe–Schmitt reaction.

純化方法Crystallise gentisic acid from hot water or *benzene/acetone. Dry it in a vacuum desiccator over silica gel. [Beilstein 10 H 384, 10 IV 1441.]

上流・下流製品情報

上流原料

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
補足説明 · 1 件

定義ChEBI: 2,5-dihydroxybenzoic acid is a dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. It has a role as a MALDI matrix material, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a human metabolite, a fungal metabolite and a mouse metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.

関連反応

73 件
反応記録を作成

関連ノート

読み込み中…