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Key Documents

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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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)
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
M Holzbauer et al.
Medical biology, 63(3), 97-116 (1985-01-01)
The intermediate and the neural lobe of the pituitary gland are innervated by two, virtually independent, groups of dopaminergic neurons which, until recently, were considered as a uniform system and referred to as the "tubero-hypophyseal dopamine system". Some aspects of

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