基本情報
- 標準SMILES
COc1cc(C(C)=O)ccc1O- InChIKey
DFYRUELUNQRZTB-UHFFFAOYSA-N- 分子式
- C9H10O3
- 平均分子量
- 166.17 g/mol
- 単同位体質量
- 166.06299418
名称と識別子
- 優先名称
- Acetovanillone
- IUPAC
- 1-(4-hydroxy-3-methoxyphenyl)ethanone
- 現地名
- 4'-ヒドロキシ-3'-メトキシアセトフェノン
- 英語名
- Acetovanillone
- 分子式
- C9H10O3
- 分子量
- 166.17
名称と別名
名称をさらに表示
データベース識別子
- CAS
498-02-2- PubChem CID
- 2214
- DTXSID
DTXSID7060097- ChEMBL
CHEMBL346919- ChEBI
CHEBI:2781- UNII
- B6J7B9UDTR
- EC Number
- 207-854-5
- Nikkaji
- J13.670K
物性
構造計算による物性
- XLogP
- 0.5
- 極性表面積
- 46.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 167
実験および物理化学的性質
Kovats Retention Index
1447;1503;1461;1448.3
1496;1491;1498.7;1480;1497;1539;1485;1498;1487;1539;1490;1491;1483;1484.1;1486.5;1482;1478.6;1484;1494
2676;2667;2606;2620;2620;2667;2664;2664;2623;2664;2640;2651.5;2637;2626;2638;2640;2640;2640.1
物理化学的性質
- 融点
- 112 · 112-115 °C (lit.)
- 沸点
- 263 · 263-265 °C/17 mmHg (lit.)
- 比重(密度)
- 1.1708 · 1.1708 (rough estimate)
- 屈折率
- 1.5101 · 1.5101 (estimate)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- アセトニトリル(微量)、クロロホルム(微量)、酢酸エチル(微量)、メタン
- 酸解離定数(Pka)
- 8.18 · 8.18±0.18(Predicted)
- 外見
- 個体
- 色
- 黄色から茶色
- 臭い (Odor)
- 100 %で。ほのかに甘いバニリン · 100.00%で。ほのかに甘いバニリン
- においのタイプ
- バニラ
- 由来生物
- synthetic
- 水溶解度
- 熱湯に溶ける
- Merck
- 14 · 14,741
- BRN
- 637373 · 637373
- Henry's Law Constant
- 6.3 · 6.3×103 mol/(m3Pa) at 25℃, McFall et al. (2020)
- 化粧品成分の機能
- スキンコンディショニング - その他
- InChI
- 1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
- InChIKey
- DFYRUELUNQRZTB-UHFFFAOYSA-N
- SMILES
- COc1cc(ccc1O)C(C)=O
- LogP
- 1.389 · 1.389 (est)
- CAS データベース
- 498 · 498-02-2(CAS DataBase Reference)
- NISTの化学物質情報
- 1 · Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)
- EPAの化学物質情報
- Acetovanillone (498-02-2)
化学的性質
化学的特性Acetovanillone is a yellowish to brown powder, soluble in alcohol, essential oils, and perfume chemicals. It is slightly soluble in water at room temperature but readily dissolves in hot water. It has a very faint, sweet odor, faintly reminiscent of vanillin, but with less spiciness and somewhat fresher notes. It occurs widely in nature, including in Orris root distillate.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 65.7% (94 of 143) of all reports.
Warning
H315 (34.3%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (34.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (33.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 143 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 94 of 143 reports by companies.;There are 7 notifications provided by 49 of 143 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
Chemical: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
法規制情報
Regulatory Information
Chemical: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AM8800000
- hs_code
- 29145000
- risk_code
- 36/37/38
- 化審法
- (3)-645
- hazard_code
- Xi
- safety_code
- 26-36
- 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
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
用途と製造
応用分野
使用Acetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.
一般的な説明Acetovanillone is an aromatic plant ketone, which is a selective inhibitor of NADPH oxidase. It is mainly secreted in the urine of mammals as the corresponding glucuronide conjugate.
調製方法
製造方法Synthetically by methylation of 3,4-Dihydroxyacetophenone. It can also be obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. It can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.
Synthetically by methylation of 3,4- Dihydroxy acetophenone. Also from Guaiacol acetate with Zinc chloride and Acetic anhydride. Can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.
純化方法Crystallise apocynin from water, or EtOH/pet ether. [Beilstein 8 IV 1814.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone.
関連反応
関連ノート
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