ゲンチシン酸
2,5-Dihydroxybenzoic acid
基本情報
- CAS
490-79-9- 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
概要
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 mouse metabolite, a fungal metabolite and a human metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.
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
- 形式電荷
- 0
- 複雑度
- 157
実験および物理化学的性質
Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals -> Metabolite of Acetylsalicylic acid
LogP
1.74
1.12
Solubility5.0 mg/mL at 5 °C
Melting Point199.5 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description
Solid; [Merck Index] Light yellow crystals; [Aldrich MSDS]
Solid
Collision Cross Section
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)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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]
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.
危険有害性情報
Regulatory Information
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%)
毒性情報
Adverse EffectsNeurotoxin - Other CNS neurotoxin
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LY3850000
- hs_code
- 29182990
- risk_code
- 22-36/37/38
- 化審法
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
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:
General Manufacturing InformationBenzoic acid, 2,5-dihydroxy-: ACTIVE
応用分野
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.
関連反応
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化合物ノート
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