Homovanillyl alcohol - Misplaced Pages

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Homovanillyl alcohol
Names

IUPAC name 4-(2-Hydroxyethyl)-2-methoxyphenol
Other names Homovanillic alcohol; MOPET; 3-Methoxy-4-hydroxyphenylethanol; 3-Methoxy-4-hydroxyphenethyl alcohol; 4-Hydroxy-3-methoxyphenethanol, 4-Hydroxy-3-methoxyphenethyl alcohol
Identifiers
CAS Number	2380-78-1
3D model (JSmol)	Interactive image
ECHA InfoCard	100.017.433
PubChem CID	16928
CompTox Dashboard (EPA)	DTXSID40178494
SMILES COC1=C(C=CC(=C1)CCO)O
Properties
Chemical formula	C₉H₁₂O₃
Molar mass	168.19 g/mol
Melting point	40-42 °C
Hazards
Flash point	113 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Homovanillyl alcohol is a metabolite of hydroxytyrosol, which in turn is a metabolite of the neurotransmitter dopamine.

References

Homovanillyl alcohol at Sigma-Aldrich

Neurotransmitter metabolic intermediates

Catecholamines

Anabolism

Phenylalanine → Tyrosine → DOPA (levodopa) → Dopamine → Norepinephrine → Epinephrine

Catabolism

Dopamine	3,4-Dihydroxyphenylacetaldehyde (DOPAL) 3,4-Dihydroxyphenylacetic acid (DOPAC) Homovanillyl alcohol Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET) 3-Methoxytyramine (3-MT) Homovanillic acid (HVA)
Norepinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) 3,4-Dihydroxymandelic acid (DHMA) Normetanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL) Vanillylmandelic acid (VMA) 3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG) 3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
Epinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) Metanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL)

Tryptophan→Serotonin

Anabolism	Tryptophan 5-Hydroxytryptophan (5-HTP)
Catabolism	5-Hydroxyindoleacetaldehyde (5-HIAL) 5-Hydroxyindoleacetic acid (5-HIAA) 5-Hydroxytryptophol (5-HTOL)

Serotonin→Melatonin

Trace amines

GABA

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See also

References