3-Hydroxy-p-anisaldehyd
Isovanillin
Grundinformationen
- CAS
621-59-0- Standard-SMILES
COc1ccc(C=O)cc1O- InChIKey
JVTZFYYHCGSXJV-UHFFFAOYSA-N- Summenformel
- C8H8O3
- Durchschnittliche Molmasse
- 152,15 g/mol
- Monoisotopische Masse
- 152,04734411
Überblick
Isovanillin is a member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase. It has a role as a HIV protease inhibitor, an antifungal agent, an antidiarrhoeal drug, an EC 1.2.3.1 (aldehyde oxidase) inhibitor, an animal metabolite and a plant metabolite. It is a member of benzaldehydes, a monomethoxybenzene and a member of phenols.
Namen und Bezeichner
- Bevorzugter Name
- Isovanillin
- IUPAC
- 3-hydroxy-4-methoxybenzaldehyde
- Lokaler Name
- 3-Hydroxy-p-anisaldehyd
- Englischer Name
- Isovanillin
- Summenformel
- C8H8O3
- Molmasse
- 152.15
Namen und Synonyme
ISOVANILLIN3-Hydroxy-4-methoxybenzaldehyde621-59-0Isovanilline5-Formylguaiacol3-Hydroxy-p-anisaldehydeBenzaldehyde, 3-hydroxy-4-methoxy-iso-Vanillin4A9N90H9X6NSC-82996RefChem:792444210-694-9
Weitere Namen anzeigen
sovanillin3-Hydroxy-4-methoxyBenzaldehyde,3-hydroxy-4-methoxy-C8H8O3NSC 82996lsovanillin
Isovanicaline3-Hydroxy-4-methoxy-benzaldehydeisovanilin3-Hydroxyanisaldehydep-Anisaldehyde, 3-hydroxy-Oxy-3 methoxy-4 benzaldehyde3-hydroxy-4-anisaldehydeMFCD00003369
Datenbank-Bezeichner
- CAS
621-59-0- PubChem CID
- 12127
- DTXSID
DTXSID7049423- ChEMBL
CHEMBL275563- ChEBI
CHEBI:193161- UNII
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 135
Experimentelle und physikochemische Eigenschaften
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP0.97
Food AdditivesFood
Endocrine DisruptorsPotential endocrine disrupting compound
Physikochemische Eigenschaften
- Schmelzpunkt
- 113 · 113-116 °C
- Siedepunkt
- 179 °C15 · 179 °C15 mm Hg(lit.)
- Dichte
- 1.2 · 1.20
- Dampfdruck
- 0 Pa · 0Pa at 20℃
- Brechungsindex
- 1.4945 · 1.4945 (estimate)
- Flammpunkt
- 179 °C/15mm · 179°C/15mm
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in acetone and methanol.
- pka
- 1 · pK1:8.889 (25°C)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 13.3% (8 of 60) of reports.
Warning
H315 (86.7%): 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 60 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationREACH registered substance: 3-hydroxy-p-anisaldehyde (EC: 210-694-9)
Hazard Classes and CategoriesSkin Irrit. 2 (86.7%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2912499000
- RTECS-Nr.
- CU6540000
- risk_code
- 36/37/38
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37-36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Verwendung und Herstellung
General Manufacturing InformationBenzaldehyde, 3-hydroxy-4-methoxy-: ACTIVE
Anwendungen
Verwenden3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis.
Darstellung
synthetischeSynthesis of isovanillin: 4-Hydroxybenzaldehyde is used as raw material, firstly react with bromine to obtain 3-bromo-4-hydroxybenzaldehyde, then react with methyl iodide to obtain 3-bromo-4-methoxybenzaldehyde, and then hydrolyzed under the action of sodium hydroxide and cuprous chloride to produce isovanillin. The yield was 64.1%.
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