2,5-다이하이드록시벤조익애씨드
2,5-다이하이드록시벤조익애씨드 · GENTISIC ACID · DHB · Gentisate · Gentisic · 2,5-Dhba · Phloretate · Gensigen
식별자 및 물리적 특성
| CAS No. | 490-79-9 |
|---|---|
| 분자식 | C7H6O4 |
| 평균 분자량 | 154.12 g/mol |
| 단동위원소 질량 | 154.02660867 g/mol |
| SMILES | O=C(O)c1cc(O)ccc1O |
| InChIKey | WXTMDXOMEHJXQO-UHFFFAOYSA-N |
| PubChem CID | 3469 |
| ChEMBL | CHEMBL1461 |
| ChEBI | CHEBI:17189 |
| EC No. | 207-718-5 |
| DTXSID | DTXSID4060078 |
| 현지명 | 2,5-다이하이드록시벤조익애씨드 |
화학 및 물리적 성질
| XLogP | 1.6 |
|---|---|
| 극성 표면적 | 77.8 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 157 |
| LogP(분배 계수) | 1.74 |
| 용해도 | 5.0 mg/mL at 5 °C알코올과 에테르에 용해됩니다. |
| 녹는점 | 199.5 °C204-208 °C(lit.) |
| 증기압 | 0.0000021 [mmHg] |
| Physical Description | Solid[Merck Index] Light yellow crystals[Aldrich MSDS] |
| Collision Cross Section | 122.67 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]125 Ų [M-H]- |
| 끓는 점 | 237.46°C (rough estimate) |
| 밀도 | 1.3725 (rough estimate) |
| 굴절률 | 1.6400 (estimate) |
| 저장 조건 | Store below +30°C. |
| pKa(산도 계수) | 2.97(at 25℃) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색~밝은 베이지 |
| pH | 3.21(1 mM solution)2.56(10 mM solution)2.01(100 mM solution) |
| 용해도 | 녹는 |
| Merck | 14,4398 |
| BRN | 2209119 |
| 화장품 원료 기능 | 피부 컨디셔닝 |
| InChI | 1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) |
| InChIKey | WXTMDXOMEHJXQO-UHFFFAOYSA-N |
| SMILES | OC(=O)c1cc(O)ccc1O |
| LogP(분배 계수) | 1.740 |
| NIST | 2,5-Dihydroxybenzoic acid(490-79-9) |
| EPA | Benzoic acid, 2,5-dihydroxy- (490-79-9) |
화학적 성질
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.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.WarningH302 (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 exposureRespiratory 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. |
|---|---|
| 규제 정보 | 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 |
| 유해성 요약 | Causes convulsions in intravenous lethal-dose studies of mice[RTECS] A skin and strong eye irritantHarmful by ingestion and skin absorptionEvidence of reproductive toxicity in experimental animals[Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (94%)Skin Irrit. 2 (94%)Eye Irrit. 2 (94%)STOT SE 3 (92.5%) |
| 유해 작용 | Neurotoxin - Other CNS neurotoxin |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | LY3850000 |
| 관세 코드 | 29182990 |
| 위험 문구(R) | 22-36/37/38 |
| 위험 표시 | Xn,Xi |
| 안전 문구(S) | 26-36-37/39 |
| 위험 참고 사항 | Harmful |
| 위험 등급 | Acute Tox. 4 Oral |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
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.
일반 설명
Aspirin metabolite.
제조 및 합성 방법
생산 방법
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.