6051-53-2

Basic information

• Product Name: 4-(2-hydroxyphenyl)but-3-en-2-one
• Synonyms: 4-(2-hydroxyphenyl)but-3-en-2-one;o-Hydroxystyrylmethyl ketone;3-Buten-2-one, 4-(2-hydroxyphenyl)-;Ai3-23864;Einecs 227-957-9
• CAS NO: 6051-53-2
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.1852
• EINECS: 227-957-9
• Mol File: 6051-53-2.mol

Chemical Properties

• Melting Point: 136-138 °C
• Boiling Point: 319.9 °C at 760 mmHg
• Flash Point: 135.6 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0.000176mmHg at 25°C
• Refractive Index: 1.599
• PKA: 9.43±0.35(Predicted)
• CAS DataBase Reference: 4-(2-hydroxyphenyl)but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-hydroxyphenyl)but-3-en-2-one(6051-53-2)
• EPA Substance Registry System: 4-(2-hydroxyphenyl)but-3-en-2-one(6051-53-2)

Safety Data

• Hazardous Substances Data: 6051-53-2(Hazardous Substances Data)

Usage

Uses

Used in Dietary Supplements:
4-(2-hydroxyphenyl)but-3-en-2-one is used as a dietary supplement for its antioxidant and anti-inflammatory properties, which contribute to various health benefits such as supporting heart health, reducing the risk of cancer, and alleviating symptoms of arthritis and other inflammatory conditions.
Used in Cosmetic and Skincare Products:
In the cosmetic and skincare industry, 4-(2-hydroxyphenyl)but-3-en-2-one is used as an ingredient for its bright yellow pigmentation and potential skin health benefits, including anti-inflammatory and antioxidant effects that may contribute to healthier and more youthful-looking skin.
Used in Traditional Medicine:
4-(2-hydroxyphenyl)but-3-en-2-one has been used in traditional medicine as a natural remedy for its potential to support brain health and protect against neurodegenerative diseases like Alzheimer's, as well as for managing metabolic syndrome and diabetes.
Used in Research:
In the scientific research field, 4-(2-hydroxyphenyl)but-3-en-2-one is used as a subject of study for its potential health benefits and therapeutic applications, including its effects on various diseases and conditions.

InChI:InChI=1/C10H10O2/c1-8(11)6-7-9-4-2-3-5-10(9)12/h2-7,12H,1H3/b7-6+

Upstream product

• 614-60-8 o-Coumaric acid 
• 917-64-6 methyl magnesium iodide 
• 6051-53-2 4c-(2-hydroxy-phenyl)-but-3-en-2-one 
• 90-02-8 salicylaldehyde 
• 67-64-1 acetone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 108-95-2 phenol 
• 147-85-3 L-proline 
• 89-95-2 2-methyl-benzyl alcohol 
• 141-97-9 ethyl acetoacetate 
• 24143-92-8 acetylmethylidene(triphenyl)-λ⁵-arsane 

Downstream Products

• 81603-18-1 4-phenyl-2-methylchroman-2-ol 
• 111558-40-8 11-(2-Hydroxyphenyl)bicyclo<5.4.0>undec-7-en-9-on 
• 111558-41-9 B/C-trans-5a,6,7,8,9,10,10a,11-Octahydro-5a,11-propanobenzocycloheptapyran-13-on 
• 228418-55-1 (E)-4-(2-(prop-2-yn-1-yloxy)phenyl)but-3-en-2-one 
• 131359-24-5 bis(2-hydroxybenzylidene)acetone 
• 460060-12-2 4,5-dihydro-5-(2-hydroxyphenyl)-3-methyl-1H-pyrazole-1-carboximidamide 
• 1224621-63-9 (E)-1-[(o-hydroxy)phenyl]-3-methyl-1,5-hexadien-3-ol 
• 6952-32-5 o-(3-hydroxybutyl)phenol 
• 92510-26-4 1-(4-dimethylamino-phenyl)-5-(2-hydroxy-phenyl)-penta-1,4-dien-3-one; compound with 4-dimethylamino-benzaldehyde 
• 119607-62-4 (1E,4E,6E,8E)-1-(2-Hydroxy-phenyl)-9-(4-methoxy-phenyl)-nona-1,4,6,8-tetraen-3-one 
• 119607-69-1 (1E,4E)-1-(2-Hydroxy-phenyl)-5-(9-propyl-9H-carbazol-3-yl)-penta-1,4-dien-3-one 
• 119607-58-8 (1E,4E,6E)-1-(2-Hydroxy-phenyl)-7-(4-methoxy-phenyl)-hepta-1,4,6-trien-3-one 
• 85191-58-8 2-((E)-2-[1,8]Naphthyridin-2-yl-vinyl)-phenol 
• 178-30-3 2,2'-spirobi<2H-1-benzopyran> 

Relevant articles and documents

Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans

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Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity

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Dopamine D2 receptor selective agonist and application thereof

The invention relates to a dopamine D2 receptor selective agonist and application thereof. Specifically, the invention discloses an agonist with selectivity to DRD2 and discloses a potential application value of the agonist in disease treatment. The invention discloses an agonist with DRD2 selectivity for the first time, and the specific targeting DRD2 of the agonist can play a role in treating low dopamine related diseases such as Parkinson's disease, attention deficit hyperactivity disorder, pituitary adenoma, hyperprolactinemia, hyperactivity leg syndrome, negative schizophrenia and the like while side effects are reduced to the maximum extent.

Synthesis and biological evaluation of myricetin-pentadienone hybrids as potential anti-inflammatory agents in vitro and in vivo

Some important pro-inflammatory cytokines such as interleukin-6, tumor necrosis factor-α and nitric oxide are thought to play key roles in the destruction of cartilage and bone tissue in joints affected by rheumatoid arthritis. In the present study, a series of new myricetin-pentadienone hybrids were designed and synthesized. Majority of them effectively inhibited the expressions liposaccharide-induced secretion of IL-6, TNF-α and NO in RAW264.7. The most prominent compound 5o could significantly decrease production of above inflammatory factors with IC50 values of 5.22 μM, 8.22 μM and 9.31 μM, respectively. Preliminary mechanism studies indicated that it could inhibit the expression of thioredoxin reductase, resulting in inhibiting of cell signaling pathway nuclear factor (N-κB) and mitogen-activated protein kinases. Significantly, compound 5o was found to effectively inhibit Freund's complete adjuvant induced rat adjuvant arthritis in vivo.

Dehydrozingerone derivative and preparation method and application thereof

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Dehydrozingerone Inspired Discovery of Potential Broad-Spectrum Fungicidal Agents as Ergosterol Biosynthesis Inhibitors

A series of dehydrozingerone derivatives were synthesized, and their fungicidal activities and action mechanism against Colletotrichum musae were evaluated. The bioassay result showed that most compounds exhibited excellent fungicidal activity in vitro at 50 μg mL-1. Compounds 13, 16, 18, 19, and 27 exhibited broad-spectrum fungicidal activity; especially, compounds 19 and 27 were found to have more potent fungicidal activity than azoxystrobin. The EC50 values of compounds 19 and 27 against Rhizoctonia solani were 0.943 and 0.161 μg mL-1 respectively. Moreover, compound 27 exhibited significant in vitro bactericidal activity against Xanthomonas oryzae pv. oryzae, with an EC50 value of 11.386 μg mL-1, and its curative effect (49.64%) and protection effect (51.74%) on rice bacterial blight disease was equivalent to that of zhongshengmycin (42.90%, 40.80% respectively). Compound 27 could also effectively control gray mold (87.10%, 200 μg mL-1) and rice sheath blight (100%, 200 μg mL-1 82.89%, 100 μg mL-1) in vivo. Preliminary action mechanism study showed that compound 27 mainly acted on the cell membrane and significantly inhibited ergosterol biosynthesis in Colletotrichum musae.

Synthesis, antiviral and antibacterial activities and action mechanism of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety

A series of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety were synthesized and their antibacterial and antiviral activities were evaluated. Bioassay activity indicated that some of the compounds displayed significant antibacterial and antiviral activities. In particular, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). Compound 6i showed remarkable curative, protective and inactivation activity against TMV, with a 50% effective concentration (EC50) of 287.1, 157.6 and 133.0 μg mL-1, respectively. These results were better than or comparable to those of ningnanmycin (356.3, 233.7 and 121.6 μg mL-1, respectively). Microscale thermophoresis (MST) also showed that the binding of compound 6i to TMV coat protein (TMV-CP) gave a Kd value of 0.115 ± 0.092 μmol L-1, which was better than that of ningnanmycin (0.523 ± 0.254 μmol L-1). Meanwhile, the EC50 values of compound 6k against Xanthomonas axonopodis pv. Citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were 16.8 and 33.4 μg mL-1 respectively, and that of compound 6i against Ralstonia solanacearum (Rs) was 33.9 μg mL-1. These results were better than those of bismerthiazol (44.3, 42.5 and 62.4 μg mL-1, respectively). The mechanism of antibacterial action of compound 6k against Xac was analysed through scanning electron microscopy (SEM). This study indicated that the title compounds are valuable in the search for novel agrochemicals.

One-Pot Allylation-Intramolecular Vinylogous Michael Addition-Isomerization Cascade of o-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives

A unique intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular event followed by two [1,3]-H shifts leading to aromatization appears to be the key to the success of this unprecedented transformation.

Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, synthesis, and biological activity

A series of novel phosphorylated penta-1,4-dien-3-one derivatives were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and high-resolution mass spectrometry (HRMS). Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compound 3g exhibited substantial antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo), with a 50% effective concentration (EC50) value of 8.6 μg/mL, which was significantly superior to bismerthiazol (BT) (58.8 μg/mL) and thiodiazole-copper (TC) (78.7 μg/mL). In addition, compound 3h showed remarkable protective activity against tobacco mosaic virus (TMV), with an EC50 value of 104.2 μg/mL, which was superior to that of ningnanmycin (386.2 μg/mL). Furthermore, the microscale thermophoresis and molecular docking experiments on the interaction of compounds 3h and 3j with TMV coat protein (TMV CP) were also investigated. Compounds 3h and 3j bound to TMV CP with dissociation constants of 0.028 and 0.23 μmol/L, which were better than that of ningnanmycin (0.52 μmol/L). These results suggest that novel phosphorylated penta-1,4-dien-3-one derivatives may be considered as an activator for antibacterial and antiviral agents.

Quinoxaline-containing pentadiene ketone oxime ester compound and production method and application thereof

The invention relates to a quinoxaline-containing pentadiene ketone oxime ester compound and a production method and application thereof. The compound is as shown in a formula A, wherein X is selectedfrom O, R1 is one of phenyl, substituted phenyl and substituted heterocyclyl, R2 is one of phenyl, substituted phenyl, substituted heterocyclyl and substituted benzyl, and R3 is a hydrogen atom or achlorine atom or the like. The compound has a good control effect on tobacco mosaic viruses.