Homovanillyl alcohol: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~400096692~~
			\| Watchedfields = changed
⚫	\|Reference=<ref> at ]</ref>
		⚫	\| verifiedrevid = 423307752
⚫	\|ImageFile=Homovanillyl alcohol.png
		⚫	\| Reference =<ref> at ]</ref>
⚫	\|ImageSize=~~200px~~
		⚫	\| ImageFile =Homovanillyl alcohol.png
⚫	\|~~IUPACName~~=4-(2-Hydroxyethyl)-2-methoxyphenol
		⚫	\| ImageSize =
⚫	\|OtherNames=Homovanillic alcohol; MOPET; 3-Methoxy-4-hydroxyphenylethanol; 3-Methoxy-4-hydroxyphenethyl alcohol; 4-Hydroxy-3-methoxyphenethanol, 4-Hydroxy-3-methoxyphenethyl alcohol
		⚫	\| PIN =4-(2-Hydroxyethyl)-2-methoxyphenol
		⚫	\| OtherNames =Homovanillic alcohol; MOPET; 3-Methoxy-4-hydroxyphenylethanol; 3-Methoxy-4-hydroxyphenethyl alcohol; 4-Hydroxy-3-methoxyphenethanol, 4-Hydroxy-3-methoxyphenethyl alcohol
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo=2380-78-1		\| CASNo =2380-78-1
	\| PubChem=16928
			\| ChEBI = 173769
	\| SMILES=COC1=C(C=CC(=C1)CCO)O
			\| ChEMBL = 3747068
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID = 16039
			\| EINECS = 219-175-1
			\| PubChem =16928
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 9A7EE8MS6A
			\| InChI = 1/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3
			\| InChIKey = XHUBSJRBOQIZNI-UHFFFAOYAP
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = XHUBSJRBOQIZNI-UHFFFAOYSA-N
			\| SMILES = Oc1ccc(cc1OC)CCO
	}}		}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula=C<sub>9</sub>H<sub>12</sub>O<sub>3</sub>		\| Formula =C<sub>9</sub>H<sub>12</sub>O<sub>3</sub>
	\| MolarMass=168.19 g/mol		\| MolarMass =168.19 g/mol
	\| Appearance=		\| Appearance =
	\| Density=		\| Density =
			\| MeltingPtC = 40 to 42
	\| MeltingPt=40-42 °C
			\| MeltingPt_notes =
	\| BoilingPt=
			\| BoilingPt =
	\| Solubility=
			\| Solubility =
	}}		}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards =
	\| ~~FlashPt~~=~~113~~ °C		\| FlashPtC = 113
			\| AutoignitionPtC =
	\| Autoignition=
			\| GHS_ref=<ref>{{cite web \|title=Homovanillyl alcohol \|url=https://pubchem.ncbi.nlm.nih.gov/compound/16928#section=Safety-and-Hazards \|website=pubchem.ncbi.nlm.nih.gov \|access-date=13 December 2021 \|language=en}}</ref>
	\| RPhrases = {{R36/37/38}}
	\| ~~SPhrases~~ = {{~~S26}} {{S36~~}}		\| GHSPictograms = {{GHS07}}
			\| GHSSignalWord = Warning
			\| HPhrases = {{H-phrases\|315\|319\|335}}
			\| PPhrases = {{P-phrases\|261\|264\|271\|280\|302+352\|304+340\|305+351+338\|312\|321\|332+313\|337+313\|362\|403+233\|405\|501}}
	}}		}}
	}}		}}
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	'''Homovanillyl alcohol''' is a ] of ], which in turn is a metabolite of the ] ].		'''Homovanillyl alcohol''' is a ] of ], which in turn is a metabolite of the ] ].

	==See also==		== See also ==
	* ]		* ]

	==References==		== References ==
	{{reflist}}		{{reflist}}

	{{Neurotransmitter metabolism intermediates}}		{{Neurotransmitter metabolism intermediates}}

	]		]
			]

	{{~~Natural-phenol~~-stub}}		{{Aromatic-stub}}

Latest revision as of 07:31, 7 January 2022

Homovanillyl alcohol
Names

Preferred 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
ChEBI	CHEBI:173769
ChEMBL	ChEMBL3747068
ChemSpider	16039
ECHA InfoCard	100.017.433
EC Number	219-175-1
PubChem CID	16928
UNII	9A7EE8MS6A
CompTox Dashboard (EPA)	DTXSID40178494
InChI InChI=1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3Key: XHUBSJRBOQIZNI-UHFFFAOYSA-N InChI=1/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3Key: XHUBSJRBOQIZNI-UHFFFAOYAP
SMILES Oc1ccc(cc1OC)CCO
Properties
Chemical formula	C₉H₁₂O₃
Molar mass	168.19 g/mol
Melting point	40 to 42 °C (104 to 108 °F; 313 to 315 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point	113 °C (235 °F; 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) 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
"Homovanillyl alcohol". pubchem.ncbi.nlm.nih.gov. Retrieved 13 December 2021.

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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Latest revision as of 07:31, 7 January 2022

See also

References