Page last updated: 2024-12-05

3-methoxy-4-hydroxyphenylethanol

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Description

3-Methoxy-4-hydroxyphenylethanol, also known as vanillyl alcohol, is a naturally occurring phenolic compound found in various plants. It is a precursor to the biosynthesis of lignin, a complex polymer that provides structural support in plant cell walls. Vanillyl alcohol has also been shown to possess antioxidant and anti-inflammatory properties, and it has been investigated for its potential therapeutic applications. It is synthesized through a series of enzymatic reactions involving the conversion of phenylalanine to vanillyl alcohol. Vanillyl alcohol has been studied for its potential as an anti-cancer agent, as it has been shown to inhibit the growth of certain cancer cell lines. It has also been explored for its potential use in the treatment of neurodegenerative diseases such as Alzheimer's disease, due to its ability to protect neurons from damage. Further research is needed to fully understand the therapeutic potential of vanillyl alcohol.'
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3-Methoxy-4-hydroxyphenylethanol: Metabolite of serotonin and norepinephrine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID16928
CHEMBL ID3747068
CHEBI ID173769
SCHEMBL ID43681
MeSH IDM0023222

Synonyms (46)

Synonym
CHEBI:173769
(4-hydroxy-3-methoxyphenyl)ethanol
4-(2-hydroxyethyl)-2-methoxyphenol
homovanillyl alcohol
4-hydroxy-3-methoxyphenylethyl alcohol
homovanillyl alcohol, 99%
2380-78-1
4-hydroxy-3-methoxyphenethanol
AKOS003382015
inchi=1/c9h12o3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11h,4-5h2,1h3
xhubsjrboqizni-uhfffaoysa-
3-methoxy-4-hydroxyphenylethanol
mopet
unii-9a7ee8ms6a
einecs 219-175-1
benzeneethanol, 4-hydroxy-3-methoxy-
4-(2-hydroxyethyl)guaiacol
9a7ee8ms6a ,
4-(2-hydroxyethyl)-2-methoxy-phenol
A816914
4-hydroxy-3-methoxyphenethyl alcohol
FT-0634232
FS-3438
SCHEMBL43681
2-(4-hydroxy-3-methoxyphenyl)-ethanol
4-(2-hydroxyethyl)-2-methoxyphenol #
homovanillin alcohol
2-(4-guaiacyl)-ethanol
guaiacyl ethanol
DTXSID40178494
CHEMBL3747068
4-hydroxy-3-methoxy-benzeneethanol
4-hydroxy-3-methoxybenzeneethanol
homovanilline alcohol
J-015221
Q5891855
mfcd00002903
CCG-356420
BCP30361
4-hydroxy-3-methoxyphenethanol pound>>4-(2-hydroxyethyl)-2-methoxyphenol
CS-0131118
HY-N7513
D95086
vanillylmethanol
VTL ,
EN300-1250800
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
methoxybenzenesAny aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1268970Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-6 secretion at 62.5 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1432861Anti-inflammatory activity in human U937-derived macrophage-like cells assessed as inhibition of LPS-induced IL-6 secretion at 125 uM preincubated for 2 hrs followed by LPS addition measured after 24 hrs by ELISA relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Synthesis and anti-inflammatory activity of isoquebecol.
AID1268978Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-1beta secretion at 62.5 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268971Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-8 secretion at 500 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1754865Antiproliferative activity against human PANC-1 cells assessed as reduction in cell growth at 100 uM incubated for 72 hrs by trypan blue assay relative to control2021Bioorganic & medicinal chemistry, 07-15, Volume: 42Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1754868Antiproliferative activity against human PC-3 cells assessed as cell death at 100 uM incubated for 72 hrs by trypan blue assay (Rvb = 3%)2021Bioorganic & medicinal chemistry, 07-15, Volume: 42Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1268976Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-1beta secretion at 250 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1432864Anti-inflammatory activity in human U937-derived macrophage-like cells assessed as inhibition of LPS-induced IL-6 secretion at 500 uM preincubated for 2 hrs followed by LPS addition measured after 24 hrs by ELISA relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Synthesis and anti-inflammatory activity of isoquebecol.
AID1268977Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-1beta secretion at 125 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268968Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-6 secretion at 250 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1754867Antiproliferative activity against human SW480 cells assessed as reduction in cell growth at 100 uM incubated for 72 hrs by trypan blue assay relative to control2021Bioorganic & medicinal chemistry, 07-15, Volume: 42Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1432860Anti-inflammatory activity in human U937-derived macrophage-like cells assessed as inhibition of LPS-induced IL-6 secretion at 250 uM preincubated for 2 hrs followed by LPS addition measured after 24 hrs by ELISA relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Synthesis and anti-inflammatory activity of isoquebecol.
AID1432862Anti-inflammatory activity in human U937-derived macrophage-like cells assessed as inhibition of LPS-induced IL-6 secretion at 62.5 uM preincubated for 2 hrs followed by LPS addition measured after 24 hrs by ELISA relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Synthesis and anti-inflammatory activity of isoquebecol.
AID1268982Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated TNF-alpha secretion at 62.5 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1754870Antiproliferative activity against human PANC-1 cells assessed as cell death at 100 uM incubated for 72 hrs by trypan blue assay relative to control2021Bioorganic & medicinal chemistry, 07-15, Volume: 42Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1268983Antiinflammatory activity in human U937-3xkB-luc cells assessed as inhibition of LPS-induced NFkappaB activation at 100 uM preincubated for 30 mins followed by LPS-stimulation measured after 6 hrs by luciferase assay relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268975Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-1beta secretion at 500 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268980Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated TNF-alpha secretion at 250 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268985Antiinflammatory activity in human U937-3xkB-luc cells assessed as inhibition of LPS-induced NFkappaB activation at 5 uM preincubated for 30 mins followed by LPS-stimulation measured after 6 hrs by luciferase assay relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268969Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-6 secretion at 125 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268973Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-8 secretion at 125 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268966Cytotoxicity against PMA-differentiated human U937 macrophages assessed as reduction in cell viability after 24 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268972Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-8 secretion at 250 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1432859Cytotoxicity against human U937-derived macrophage-like cells assessed as reduction in cell viability after 24 hrs by MTT assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Synthesis and anti-inflammatory activity of isoquebecol.
AID1268984Antiinflammatory activity in human U937-3xkB-luc cells assessed as inhibition of LPS-induced NFkappaB activation at 20 uM preincubated for 30 mins followed by LPS-stimulation measured after 6 hrs by luciferase assay relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1754866Antiproliferative activity against human PC-3 cells assessed as reduction in cell growth at 100 uM incubated for 72 hrs by trypan blue assay relative to control2021Bioorganic & medicinal chemistry, 07-15, Volume: 42Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines.
AID1268967Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-6 secretion at 500 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268981Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated TNF-alpha secretion at 125 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1268979Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated TNF-alpha secretion at 500 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
AID1432863Anti-inflammatory activity in human U937-derived macrophage-like cells assessed as inhibition of LPS-induced IL-6 secretion at 31.25 uM preincubated for 2 hrs followed by LPS addition measured after 24 hrs by ELISA relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Synthesis and anti-inflammatory activity of isoquebecol.
AID1268974Antiinflammatory activity in PMA-differentiated human U937 cells assessed as inhibition of LPS-stimulated IL-8 secretion at 62.5 uM preincubated for 2 hrs followed by LPS-stimulation measured after 24 hrs by ELISA relative to control2016Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2
Anti-inflammatory properties of quebecol and its derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-199037 (75.51)18.7374
1990's4 (8.16)18.2507
2000's3 (6.12)29.6817
2010's2 (4.08)24.3611
2020's3 (6.12)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.78

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.78 (24.57)
Research Supply Index3.93 (2.92)
Research Growth Index4.72 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.04%)5.53%
Reviews2 (4.08%)6.00%
Case Studies1 (2.04%)4.05%
Observational0 (0.00%)0.25%
Other45 (91.84%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]