3-Hydroxy-p-anisaldehyd

Bezeichnung:3-Hydroxy-p-anisaldehyd

CAS-Nr621-59-0

Englisch Name:Isovanillin

CBNumberCB0705725

SummenformelC8H8O3

Molgewicht152.15

MOL-Datei621-59-0.mol

Synonyma

3-Hydroxy-p-anisaldehyd

3-Hydroxy-p-anisaldehyd physikalisch-chemischer Eigenschaften

Schmelzpunkt	113-116 °C
Siedepunkt	179 °C15 mm Hg(lit.)
Dichte	1.20
Dampfdruck	0Pa at 20℃
Brechungsindex	1.4945 (estimate)
Flammpunkt	179°C/15mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Soluble in acetone and methanol.
pka	pK1:8.889 (25°C)
Aggregatzustand	crystalline
Farbe	faintly brown
Wasserlöslichkeit	2.27g/L at 20℃
Sensitive	Air Sensitive
BRN	1073021
InChIKey	JVTZFYYHCGSXJV-UHFFFAOYSA-N
LogP	0.95 at 20℃
CAS Datenbank	621-59-0(CAS DataBase Reference)
NIST chemische Informationen	Benzaldehyde, 3-hydroxy-4-methoxy-(621-59-0)
EPA chemische Informationen	Benzaldehyde, 3-hydroxy-4-methoxy- (621-59-0)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36/37-36
WGK Germany	3
RTECS-Nr.	CU6540000
Hazard Note	Irritant
TSCA	Yes
HS Code	29124900

Gefahreninformationscode (GHS)

Isovanillin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Light Tan Cyrstalline Solid
Verwenden
3-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.
Application
Isovanillin is a kind of fragrance and isomer of vanillin. it has unique properties than vanillin, its fragrance can change with the change of ambient temperature, so it is especially suitable for special cosmetics and some special fragrance industries. Isovanillin is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid, which could make it a candidate drug for use in alcohol aversion therapy.
synthetische
Synthesis 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%.
Definition
ChEBI: 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 an EC 1.2.3.1 (aldehyde oxidase) inhibitor, a plant metabolite, an antidiarrhoeal drug, an antifungal agent, a HIV protease inhibitor and an animal metabolite. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes.
Synthesis Reference(s)
The Journal of Organic Chemistry, 45, p. 1596, 1980 DOI: 10.1021/jo01297a010
Allgemeine Beschreibung
3-Hydroxy-4-methoxybenzaldehyde on condensation with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide yields Schiff-bases. It undergoes condensation reaction with1-azabicyclo[2.2.2]octan-3-one to give (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one.
Flammability and Explosibility
Not classified
target
5-HT Receptor | AChR
Source
Isovanillin is a natural product found in many plant species like Pluchea sagittalis, Pycnocycla spinose, Mondia whitei, Benincasa hispida, Arum Palaestinum, Thalictrum przewalskii, Valeriana officinalis var. latifolia[1].
läuterung methode
Crystallise isovaniline from H2O or *C6H6. The oxime has m 147o. [Beilstein 8 IV 1764.]
Einzelnachweise
[1] Ana C. de Carvalho . “Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers.” Bioorganic Chemistry 83 (2019): Pages 205-213.
[2] V. Balachandran , K. Parimala. “Vanillin and isovanillin: Comparative vibrational spectroscopic studies, conformational stability and NLO properties by density functional theory calculations.” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 95 (2012): Pages 354-368.

Isovanillin Upstream-Materialien And Downstream Produkte

3-Hydroxy-p-anisaldehyd Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

621-59-0, Isovanillin Verwandte Suche:

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