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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:
2380-78-1
Molecular Weight:
168.19
EC Number:
219-175-1
MDL number:
MFCD00002903
UNSPSC Code:
12352100
PubChem Substance ID:
24848920
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

Related Categories

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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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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
D J Edwards et al.
Biochemical pharmacology, 34(8), 1255-1263 (1985-04-15)
The effects in rats of intraventricular injections of 6-hydroxydopamine (6-OHDA) on the urinary excretion 1-3 weeks later of 3-methoxy-4-hydroxyphenethylene glycol (MHPG), 3,4-dihydroxyphenethanol (DHPE), 3-methoxy-4-hydroxyphenethanol (MHPE), p-hydroxyphenylglycol (pHPG), homovanillic acid (HVA) and 3,4-dihydroxyphenylacetic acid (DOPAC) were examined. The excretion of MHPG
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
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
H H Miller et al.
European journal of pharmacology, 78(1), 33-44 (1982-02-19)
A comparison of the in vivo biochemical actions of the psychotomimetic central stimulants, d-amphetamine (d-AMPH) and amfonelic acid (AFA), on the metabolism of rat striatal newly synthesized [3H]dopamine (DA) was made by pulse labeling with [3H]tyrosine. No evidence for the
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