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148830

Sigma-Aldrich

Homovanillyl alcohol

99%

Synonym(s):

4-Hydroxy-3-methoxyphenethanol, 4-Hydroxy-3-methoxyphenethyl alcohol

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About This Item

Linear Formula:
HOC6H3(OCH3)CH2CH2OH
CAS Number:
Molecular Weight:
168.19
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

mp

40-42 °C (lit.)

SMILES string

COc1cc(CCO)ccc1O

InChI

1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3

InChI key

XHUBSJRBOQIZNI-UHFFFAOYSA-N

General description

Homovanillyl alcohol is a key component of Queen mandibular pheromone.

Application

Homovanillyl alcohol was used in the preparation of galactosides.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Guangmiao Fu et al.
Current medicinal chemistry, 15(25), 2592-2613 (2008-10-16)
Natural products have long been regarded as excellent sources for drug discovery given their structure diversity and wide variety of biological activities. Phenylethanoid glycosides are naturally occurring compounds of plant origin and are structurally characterized with a hydroxyphenylethyl moiety to
D F Sharman et al.
Comparative biochemistry and physiology. C, Comparative pharmacology and toxicology, 75(2), 217-222 (1983-01-01)
Following the i.v. administration of 3,4-dihydroxyphenylethylamine (dopamine) to sheep, 3,4-dihydroxyphenylethanol and 3,4-dihydroxyphenylacetic acid rapidly appeared in the blood. 3,4-Dihydroxyphenylethanol can be formed from dopamine by blood plasma of ruminants in vitro. It is suggested that this plasma enzyme system might
K Racké et al.
Journal of neurochemistry, 46(3), 745-752 (1986-03-01)
Isolated rat neurointermediate lobes were incubated in vitro. The release of 3,4-dihydroxyphenylethylamine (dopamine, DA), dihydroxyphenylacetic acid (DOPAC), homovanillic acid (HVA), and methoxyphenylethanol (MOPET) was determined by HPLC with electrochemical detection. Under resting conditions, the outflow of metabolites was 35-50 times
Effects of L-DOPA on the excretion of alcoholic metabolites of catecholamines and trace amines in rat and human urine.
D J Edwards et al.
Biochemical medicine, 25(2), 135-148 (1981-04-01)
M Phillippe et al.
American journal of obstetrics and gynecology, 143(7), 782-787 (1982-08-01)
Previous investigation has demonstrated biologically significant concentrations of catecholamines in amniotic fluid, which increase with gestation. The half life, metabolic clearance rate, and metabolic fate of these hormones in the amniotic compartment are yet to be established. This study was

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