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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.)

functional group

hydroxyl

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

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G Mårdh et al.
Biochemistry, 25(23), 7279-7282 (1986-11-18)
The class I human liver alcohol dehydrogenases (ADHs) catalyze the interconversion of the intermediary alcohols and aldehydes of dopamine metabolism in vitro, whereas those of the class II and class III do not. The individual, homogeneous class I isozymes oxidize
G Wik
The Journal of endocrinology, 144(3), 425-429 (1995-03-01)
Plasma cortisol and serum 3-methoxy-4-hydroxyphenylethyl glycol (MHPG) were determined before and after 5-6 weeks of neuroleptic treatment in patients with schizophrenia. Following drug treatment both plasma cortisol and serum MHPG levels in patients decreased and plasma cortisol levels were also
D J Edwards et al.
Journal of neurochemistry, 36(5), 1641-1647 (1981-05-01)
We have investigated the effects of 3, 4-dihydroxyphenylalanine (L-DOPA) and its deuterated analogue on the concentrations of alcoholic metabolites of catecholamines in rat brain by means of gas chromatography/mass spectrometry with selected-ion monitoring. Whole brain concentrations of the two neutral
Vanina Vergoz et al.
Science (New York, N.Y.), 317(5836), 384-386 (2007-07-21)
Queen mandibular pheromone (QMP) has profound effects on dopamine signaling in the brain of young worker honey bees. As dopamine in insects has been strongly implicated in aversive learning, we examined QMP's impact on associative olfactory learning in bees. We
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

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