シリンガアルデヒド
Syringaldehyde
基本情報
- CAS
134-96-3- 標準SMILES
COc1cc(C=O)cc(OC)c1O- InChIKey
KCDXJAYRVLXPFO-UHFFFAOYSA-N- 分子式
- C9H10O4
- 平均分子量
- 182.17 g/mol
- 単同位体質量
- 182.0579088
概要
Syringaldehyde is a hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. It has a role as a hypoglycemic agent and a plant metabolite. It is a hydroxybenzaldehyde and a dimethoxybenzene.
名称と識別子
- 優先名称
- Syringaldehyde
- IUPAC
- 4-hydroxy-3,5-dimethoxybenzaldehyde
- 現地名
- シリンガアルデヒド
- 英語名
- Syringaldehyde
- 分子式
- C9H10O4
- 分子量
- 182.17
名称と別名
SYRINGALDEHYDE134-96-34-Hydroxy-3,5-dimethoxybenzaldehyde3,5-Dimethoxy-4-hydroxybenzaldehydeSyringic aldehydeSyringylaldehydeBenzaldehyde, 4-hydroxy-3,5-dimethoxy-SyringealdehydeGallaldehyde 3,5-dimethyl ether2ZR01KTT21NSC-411532,6-DIMETHOXY-4-FORMYLPHENOL
名称をさらに表示
シリンガアルデヒドガロアルデヒド3,5-ジメチルエーテル3,5-ジメトキシ-4-ヒドロキシベンズアルデヒド4-ヒドロキシ-3,5-ジメトキシベンズアルデヒドシリングアルデヒド3，5-ジメトキシ-4-ヒドロベンズアルデヒド3，5ジメトキシ4ヒドロベンズアルデヒド3,5‐ジメトキシ‐4‐ヒドロキシベンズアルデヒドシリングアルデヒド, 98+%Lilac aldehydeFEMA 4049SYRINGA ALDEHYDESyringSyringaL
DTXSID2059643FEMA NO. 4049CHEBI:67380SYALRefChem:187004DTXCID60341824-H-3,5-DMBA205-167-5
データベース識別子
- CAS
134-96-3- PubChem CID
- 8655
- DTXSID
DTXSID2059643- ChEMBL
CHEMBL225303- ChEBI
CHEBI:67380- UNII
- 2ZR01KTT21
- EC Number
- 205-167-5
- Nikkaji
- J5.601D
物性
構造計算による物性
- XLogP
- 0
- 極性表面積
- 55.8 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 4
- 回転可能結合数
- 3
- 重原子数
- 13
- 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
SpringerMaterials PropertiesChemical shift
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Insoluble in water
Soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Physical Description
Pale yellow solid; [Merck Index]
Very pale green needles; Alcoholic aroma
物理化学的性質
- 融点
- 110 · 110-113 °C(lit.)
- 沸点
- 192 · 192-193 °C14 mm Hg(lit.)
- 比重(密度)
- 1.013 · 1.013
- 屈折率
- 1.45 · 1.4500 (estimate)
- FEMA
- 4049 · 4049 | 4-HYDROXY-3,5,-DIMETHOXY BENZALDEHYDE
- 闪点
- 192 · 192-193°C/14mm
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- クロロホルム、メタノール（微量）
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 7.8 · 7.80±0.23(Predicted)
- 色
- 薄黄緑色～褐色
- 臭い (Odor)
- 100 %で。マイルドプラスチックウッディトンカスイート · 100.00%で。マイルドプラスチックウッディトンカスイート
- においのタイプ
- 緑
- 由来生物
- synthetic
- 水溶解度
- 非常に溶けにくい
- Merck
- 14 · 14,9015
- JECFA Number
- 1878 · 1878
- BRN
- 784514 · 784514
- Henry's Law Constant
- 3.7 · 3.7×105 mol/(m3Pa) at 25℃, McFall et al. (2020)
- 安定性
- 吸湿性
- 主な用途
- 洗浄剤化粧品フレーバーそして香料食品および飲料パーソナルケア
- InChI
- 1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
- InChIKey
- KCDXJAYRVLXPFO-UHFFFAOYSA-N
- SMILES
- COc1cc(C=O)cc(OC)c1O
- LogP
- 1.3 · 1.30
- CAS データベース
- 134 · 134-96-3(CAS DataBase Reference)
- NISTの化学物質情報
- 4 · Benzaldehyde, 4-hydroxy-3,5-dimethoxy-(134-96-3)
- EPAの化学物質情報
- Syringaldehyde (134-96-3)
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
H302 (97.6%): 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 1484 reports by companies from 18 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: Benzaldehyde, 4-hydroxy-3,5-dimethoxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
REACH registered substance: 4-hydroxy-3,5-dimethoxybenzaldehyde (EC: 205-167-5)
Benzaldehyde, 4-hydroxy-3,5-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes altered sleep time (including change in righting reflex) in intraperitoneal lethal-dose studies of mice (LD50 = 1,000 mg/kg); [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (97.6%)
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CU5760000
- hs_code
- 29124900
- risk_code
- 22-36/37/38
- 化審法
- (3)-1207
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- 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
用途と製造
UsesWidely distributed in plants. [Merck Index] Used as flavoring agent or adjuvant; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationBenzaldehyde, 4-hydroxy-3,5-dimethoxy-: ACTIVE
応用分野
用途有機合成原料。
説明Syringaldehyde is an important constituent of many plant isolates and has widespread occurrence in wood products. It can be easily converted to trimethoxy-benzaldehyde which is an essential intermediate of the antibacterial drug trimethoprim. It is also used in the colorimetric determination of free chlorine in water.
天然物の起源Reported found in pineapple, beer, wine, grape brandy, rum, many different whisky products, sherry, roasted barley and hardwood smoke
使用Syringaldehyde is used in biological studies for the isolation and structural characterization of milled wood lignin, dioxane lignin, and cellulolytic lignin preparation from Brewer''s spent grain.
一般的な説明Syringaldehyde is an aromatic phenolic aldehyde and a degradation product of lignin. It exhibits antioxidant activity and is reported to inhibit prostaglandin synthetase enzyme. The synthetic form of syringaldehyde is commercially used in pharmaceuticals, food, cosmetics, textiles, pulp and paper industries.
調製方法
製造方法Vanillin is converted to 5-iodovanillin, which is treated with sodium methoxide to form 4-hydroxy-3,5- dimethyxybenzaldehyde.
純化方法Crystallise syringaldehyde from pet ether. [Beilstein 8 H 391, 8 IV 2718.]
上流・下流製品情報
上流原料
下流製品
補足説明
定義ChEBI: A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.
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