4'-ヒドロキシ-3'-メトキシアセトフェノン

Acetovanillone

HCID 2214CAS 498-02-2

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

Acetovanilloneapocynin498-02-24'-Hydroxy-3'-methoxyacetophenone1-(4-Hydroxy-3-methoxyphenyl)ethanoneAcetoguaiaconeApocynine4-Acetyl-2-methoxyphenolAcetoguaiacon1-(4-hydroxy-3-methoxyphenyl)ethan-1-oneEthanone, 1-(4-hydroxy-3-methoxyphenyl)-4-Hydroxy-3-methoxyphenyl methyl ketone
名称をさらに表示
4'-ヒドロキシ-3'-メトキシアセトフェノンアセトバニロンアポシニンアセトバニルロン4′-ヒドロキシ-3′-メトキシアセトフェノンACETOVANILLONAcetovaniloneApocynin (Acetovanillone)3'-METHOXY-4'-HYDROXYACETOPHENONE
B6J7B9UDTRNSC-209524DTXSID7060097CHEBI:2781RefChem:552432DTXCID1040740207-854-54-HYDROXY-3-METHOXYACETOPHENONE

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

実験および物理化学的性質

Kovats Retention Index · 3 件

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
化学的性質 · 1 件

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 · 6 件

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 · 3 件

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

Hazard Classes and CategoriesSkin Irrit. 2 (34.3%);Eye Irrit. 2 (34.3%);STOT SE 3 (33.6%)

法規制情報

Regulatory Information · 3 件

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

化学と産業

薬理情報

MeSH Pharmacological Classification · 3 件

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

Use ClassificationFragrance Ingredients
General Manufacturing InformationEthanone, 1-(4-hydroxy-3-methoxyphenyl)-: ACTIVE

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 · 3 件

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.]

サプライヤー50 社

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韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
補足説明 · 1 件

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

225 件

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