Page last updated: 2024-12-07

1-(2,4-Dihydroxyphenyl)-1-butanone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

You're asking about **1-(2,4-Dihydroxyphenyl)-1-butanone**, which is more commonly known as **vanillyl butyl ketone (VBK)**.

**VBK** is a naturally occurring compound found in various plants, including vanilla beans. It is a **phenylpropanoid**, meaning it belongs to a class of organic compounds derived from phenylalanine.

**Importance in Research:**

**1. Biological Activity:**

* **Antioxidant:** VBK possesses potent antioxidant properties, which can protect cells from damage caused by free radicals. This makes it a potential therapeutic agent for various conditions like cancer, inflammation, and neurodegenerative diseases.
* **Anti-Inflammatory:** Studies have shown that VBK has anti-inflammatory effects, potentially modulating the inflammatory response and contributing to disease management.
* **Neuroprotective:** Research suggests that VBK may possess neuroprotective effects, potentially mitigating neuronal damage in conditions like Alzheimer's disease and Parkinson's disease.
* **Anti-Cancer:** VBK has shown some anticancer activity in preclinical studies, possibly by inhibiting tumor growth and inducing apoptosis (programmed cell death) in cancer cells.

**2. Chemical Properties:**

* **Versatile Building Block:** VBK's structure makes it a valuable building block for synthesizing various organic compounds with potential applications in pharmaceuticals, agrochemicals, and other fields.
* **Flavor and Fragrance:** As a component of vanilla, VBK contributes to its characteristic aroma and flavor. This makes it relevant in food, beverage, and cosmetic industries.

**3. Environmental Applications:**

* **Bioremediation:** VBK has shown promise in bioremediation processes, particularly in degrading environmental pollutants like pesticides and heavy metals.

**4. Potential for Drug Development:**

VBK's diverse biological activities have sparked interest in developing it or its derivatives into therapeutic drugs for various diseases. Researchers are exploring its potential for treating conditions like:

* Alzheimer's disease
* Parkinson's disease
* Cancer
* Inflammatory diseases

**However, it is crucial to note that research on VBK is still ongoing, and further studies are needed to fully understand its therapeutic potential, safety, and efficacy.**

Overall, 1-(2,4-Dihydroxyphenyl)-1-butanone (VBK) is a promising compound with diverse biological activities, making it an active area of research in various fields, including medicine, chemistry, and environmental science.

Cross-References

ID SourceID
PubMed CID78103
CHEMBL ID1727046
CHEBI ID173857
SCHEMBL ID3662473

Synonyms (37)

Synonym
CHEBI:173857
1-(2,4-dihydroxyphenyl)butan-1-one
1-(2,4-dihydroxyphenyl)-1-butanone
4-butanoylresorcinol
unii-kn887b5y9h
einecs 224-508-9
2',4'-dihydroxybutyrophenone
nsc 43564
kn887b5y9h ,
4390-92-5
nsc-43564
nsc43564
mls000736583 ,
smr000528206
NCGC00246811-01
AKOS006275585
1-(2,4-dihydroxy-phenyl)-butan-1-one
SCHEMBL3662473
4-butyryl- 1,3-dihydroxybenzene
IWADIQGGJLCBRK-UHFFFAOYSA-N
4-butyryl-1,3-dihydroxybenzene
CHEMBL1727046
1-butanone, 1-(2,4-dihydroxyphenyl)-
DTXSID80195983
4-butyrylresorcinol
resobutyrophenone
2,4-dihydroxybutyrophenone
FT-0762959
mfcd01098941
AS-10387
AMY7206
C75183
butyrophenone, 2',4'-dihydroxy-
4-propionyl-1,3-benzenediol
A872623
CS-0152469
SY108460
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic 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]

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.12200.035520.977089.1251AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1150147Inhibition of aminopyrine demethylase activity of mixed function oxidase system in Wistar rat liver microsomes assessed as conversion of aminopyrine to 4-aminoantipyrine after 20 mins1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
AID1150146Inhibition of aniline hydroxylase activity of mixed function oxidase system in Wistar rat liver microsomes assessed as conversion of aniline to p-aminophenol after 10 mins1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]