3,4-ジヒドロキシ安息香酸
Protocatechuic Acid
基本情報
- CAS
99-50-3- 標準SMILES
O=C(O)c1ccc(O)c(O)c1- InChIKey
YQUVCSBJEUQKSH-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
3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor, an antineoplastic agent, a plant metabolite, a human xenobiotic metabolite and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is a dihydroxybenzoic acid and a member of catechols. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate.
名称と識別子
- 優先名称
- Protocatechuic Acid
- IUPAC
- 3,4-dihydroxybenzoic acid
- 現地名
- 3,4-ジヒドロキシ安息香酸
- 英語名
- Protocatechuic acid
- 分子式
- C7H6O4
- 分子量
- 154.12
名称と別名
3,4-DIHYDROXYBENZOIC ACIDprotocatechuic acid99-50-3Protocatehuic acid4-Carboxy-1,2-dihydroxybenzene4,5-Dihydroxybenzoic acidDTXSID402121236R5QJ8L4BFEMA NO. 4430NSC-16631DTXCID601212CHEBI:36062
名称をさらに表示
3,4-ジヒドロキシ安息香酸ピロカテコール-p-カルボン酸プロトカテク酸カテコール-p-カルボン酸3,4-ジヒドロキシベンゼンカルボン酸4-カルボキシピロカテコールプロトカテキュ酸3,4-ジヒドロキシ安息香酸(プロトカテキュ酸)プロトカテキユ酸 n-水和物カテコール-4-カルボン酸ピロカテコール-4-カルボン酸3,4‐ジヒドロキシ安息香酸プロトカテク酸, 100 µg/mL in AcCNコネリルアルコールProtocatechoic AcidHypogallic acid3,4-DihydroxybenzoicPROTOCATECHUIC ACID(P)Protocatechuic aci3,4-Dihydroxybenzoic acid,97%Pyrocatechol-p-carboxylic acid
RefChem:25857202-760-0protocatechuateBenzoic acid, 3,4-dihydroxy-MFCD000025093,4-Dihydroxy Benzoic AcidCarbohydroquinonic acid1ykp
物性
構造計算による物性
- XLogP
- 1.1
- 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 ClassesBiological Agents -> Plant Oils and Extracts
DrugsPharmaceuticals -> Listed in ZINC15
LogP
0.86
0.99
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
18.2 mg/mL at 14 °C
Soluble
Soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point221 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description
White to brownish solid; Discolored by air; [Merck Index]
Solid
Light brown solid
Dissociation Constants4.26 (at 25 °C)
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
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 140 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzoic acid, 3,4-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses other liver changes and multiple enzyme effects in 28-day intermittent oral studies of rats; Intraperitoneal LD50 (mouse) > 800 mg/kg; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
安全データ
- wgk
- 3
- rtecs
- UL0560000
- hs_code
- 29182990
- risk_code
- 36/37/38
- 化審法
- (3)-1616
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/MetabolitesProtocatehuic acid is a known human metabolite of 3,4-dihydroxyphenylacetic acid.
MeSH Pharmacological ClassificationAgents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Tissue LocationsFibroblasts
用途と製造
Uses
Present in wheat grains and many other plants; [Merck Index]
Synthetic Polymer MALDI Matrix Compounds
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
応用分野
解説プロトカテク酸，プロトカテクサン，モクレン科シキミ属，そのほかの植物中に存在する．カテコールと炭酸アンモニウムを水中で加熱してカルボキシル化するか，バニリン酸を脱メチル化するなどの方法で得られる．結晶．分解点199 ℃．水から再結晶したものは1分子の水和水を含む．エタノール，エーテル，熱水に可溶．塩化鉄(Ⅲ)により緑色を呈する．芳香族アミノ酸の微生物による代謝中間産物．エチルエステルは食品用抗酸化剤に用いられる．
用途医薬・香料原料。
用途医薬.香料原料。
使用3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).
一般的な説明Protocatechuic acid belongs to the class of polyphenolic compounds, which can be generally isolated from the dried flower of roselle. It can serve as a potential candidate possessing anticancer property, which can be involved in suppressing the growth of human promyelocytic leukemia HL-60 cells.
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上流原料
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