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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

Quality Level

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
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)
K Fukuhara et al.
Journal of neuroendocrinology, 8(1), 65-72 (1996-01-01)
We compared sympathoadrenal responses to intermittent cold (SART) stress (in which cold exposure is interrupted by 4-hourly intervals daily at room temperature) with those to continuous cold (-3 degrees C) stress. Plasma levels of dihydroxyphenylalanine (DOPA), catecholamines and their metabolites
Kyle T Beggs et al.
Current biology : CB, 19(14), 1206-1209 (2009-06-16)
Queen mandibular pheromone (QMP) is produced by honey bee queens and used to regulate the behavior and physiology of their nestmates. QMP has recently been shown to block aversive learning in young worker bees, an effect that can be mimicked

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