3,4-dihydroxyacetophenone
4-acetopyrocatechol
Identification
| Name | 3,4-dihydroxyacetophenone |
| CAS Number | 1197-09-7 |
| FDA UNII | 07OQ35LVBK |
| Molecular Formula | C8 H8 O3 |
| Molecular Weight | 152.14936000 |
| MDL Number | MFCD00016439 |
| Nikkaji Number | J7.452G |
| XlogP3 | 1.50 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 372.41 °C. @ 760.00 mm Hg (est) |
| Flash Point | 380.00 °F. TCC ( 193.20 °C. ) (est) |
| logP (o/w) | 1.056 (est) |
| Soluble in | water, 6.943e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intravenous-mouse LD50 235 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for 3,4-dihydroxyacetophenone usage levels up to | not for fragrance use. |
| Recommendation for 3,4-dihydroxyacetophenone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
acetopyrocatechol
4-
acetopyrocatechol
1-
acetyl-3,4-dihydroxybenzene
4-
acetylpyrocatechol
3`,4`-
dihydroxyacetophenone
3',4'-
dihydroxyacetophenone
1-(3,4-
dihydroxyphenyl)ethan-1-one
1-(3,4-
dihydroxyphenyl)ethanone
ethanone, 1-(3,4-dihydroxyphenyl)-
1-[3,4-bis(
oxidanyl)phenyl]ethanone
PubMed:
Effect of 3,4-Dihydroxyacetophenone on Endothelial Dysfunction in Streptozotocin-induced Type 2 Diabetic Rats.
PubMed:
Triggered pH/redox responsive release of doxorubicin from prepared highly stable graphene with thiol grafted Pluronic.
PubMed:
Successful stabilization of functionalized hybrid graphene for high-performance antimicrobial activity.
PubMed:
Effects of 3,4-dihydroxyacetophenone on the hypercholesterolemia-induced atherosclerotic rabbits.
PubMed:
Autotoxicity and allelopathy of 3,4-dihydroxyacetophenone isolated from Picea schrenkiana needles.
PubMed:
An efficient and selective way to new highly functionalized coronands or spiro derivatives using ultrasonic irradiation.
PubMed:
Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds.
PubMed:
[3,4-dihydroxyacetophenone inhibits proliferation of human pulmonary artery smooth muscle cells induced by focal adhesion kinase].
PubMed:
Quantitative determination of catecholic degradation products from insect sclerotized cuticles.
PubMed:
Inflammation pro-resolving potential of 3,4-dihydroxyacetophenone through 15-deoxy-delta12,14-prostaglandin J2 in murine macrophages.
PubMed:
Involvement of tyrosine residues, N-terminal amino acids, and beta-alanine in insect cuticular sclerotization.
PubMed:
Aspects of cuticular sclerotization in the locust, Scistocerca gregaria, and the beetle, Tenebrio molitor.
PubMed:
Antimelanogenic activity of 3,4-dihydroxyacetophenone: inhibition of tyrosinase and MITF.
PubMed:
Dual effect of 3,4-dihydroxyacetophenone on LPS-induced apoptosis in RAW264.7 cells by modulating the production of TNF-alpha.
PubMed:
Effect of 3, 4-dihydroxyacetophenone on Na+, K+ -ATPase activity of injured mitochondria and the oxygen consumption of brain cells of rat.
PubMed:
Effects of 3,4-dihydroxyacetophenone on cytosolic calcium in pulmonary artery endothelial and smooth muscle cells during acute hypoxia.
PubMed:
Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid.
PubMed:
[The effects of 3,4-dihydroxyacetophynone on the activity of nitric oxide synthetase in placental vascular endothelial cells and smooth muscle cells and on the level of endothelin-1 in plasma from pregnancy-induced hypertension patients].
PubMed:
Structure and kinetics of formation of catechol complexes of ferric soybean lipoxygenase-1.
PubMed:
[Uteroplacental blood flow monitoring by color Doppler flow imaging in pregnancy induced hypertension].
PubMed:
[Therapeutical mechanism of 3,4 dihydroxyacetophenone in treating chronic obstructive pulmonary disease].
PubMed:
[Effects of dihydroxyacetophenone on pulmonary hemodynamics and plasma ANP as well as cAMP/cGMP level in patients with chronic obstructive pulmonary disease].
PubMed:
Effects of 3,4-dihydroxyacetophenone (3,4-DHAP) on hypoxic pulmonary and systemic vascular response in dogs.
PubMed:
[Effect of 3,4-dihydroxyacetophenone on phospholipid components of platelet membrane in aged rats].
PubMed:
The utero-placental circulation, eugenics and the prevention and treatment of high risk pregnancies.
PubMed:
Effects of 3,4-dihydroxyacetophenone on hypoxic vasoconstriction in isolated pulmonary and basilar arterial rings.
PubMed:
[Effect of 3,4-dihydroxyacetophenone treatment on intrauterine growth retardation].
PubMed:
[Effect of 3,4-dihydroxyacetophenone on platelet aggregation in normal pregnancy and pregnancy induced hypertension].
PubMed:
The mechanism of tyrosinase-catalysed oxidative decarboxylation of alpha-(3,4-dihydroxyphenyl)-lactic acid.
PubMed:
4-alkyl-o-quinone/2-hydroxy-p-quinone methide isomerase from the larval hemolymph of Sarcophaga bullata. I. Purification and characterization of enzyme-catalyzed reaction.
PubMed:
Biosynthesis of dehydro-N-acetyldopamine by a soluble enzyme preparation from the larval cuticle of Sarcophaga bullata involves intermediary formation of N-acetyldopamine quinone and N-acetyldopamine quinone methide.
PubMed:
Effects of 3,4-dihydroxyacetophenone on the biosynthesis of TXA2 and PGI2 in human placental villus and umbilical artery segments in vitro.
PubMed:
[Biosynthesis of prostaglandin endoperoxide intermediates and its application].
PubMed:
Metabolism of aromatic plant ketones in rats: acetovanillone and paeonol.
PubMed:
[Dihydroxyacetophenone and dihydroxyphenyllactic acid increased blood flow in rat liver microcirculation].
PubMed:
[Effect of 3,4-dihydroxyacetophenone on TXA2 release from rabbit platelets].
PubMed:
[The antioxidant action of 3,4-dihydroxyacetophenone].
PubMed:
[Effects of 3,4-dihydroxyacetophenone (DHAP) on electrical and mechanical activities in the isolated myocardium].
PubMed:
[Effect of 3,4-dihydroxyacetophenone on the membrane fluidity of platelets by fluorescence polarization analysis].
PubMed:
Synthesis of pungenin, a foliar constituent of some spruce species, and investigation of its efficacy as a feeding deterrent for spruce budworm [Choristoneura fumiferana (Clem.)].
PubMed:
[Effect of 3,4-dihydroxyacetophenone on the generation of PGI2-like substances in the rat aorta].
PubMed:
[Effect of 3,4-dihydroxyacetophenone on rabbit platelet function].
PubMed:
[Effect of Qingxintong on exercise ECG and cardiac function in patients with angina pectoris].
PubMed:
[Effects of 3,4-dihydroxyacetophenone in shortening of action potential duration of cardiac cells (author's transl)].
PubMed:
Phase I clinical study of 2-(dimethylamino)-3',4'-dihydroxyacetophenone, hydrochloride (NSC-62512).
PubMed:
[Glycosidic derivatives of some pharmacologically active amines and alkaloids. 3. Preparation of glycosidic derivatives of 3,4-dihydroxyacetophenone].