4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE

Base Information

• Chemical Name: 4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE
• CAS No.: 1080-12-2
• Molecular Formula: C11H12 O3
• Molecular Weight: 192.214
• Hs Code.: 2914509090
• DSSTox Substance ID: DTXSID2061480
• Wikidata: Q81989495
• Mol file: 1080-12-2.mol

Synonyms:3-Methoxy-4-hydroxybenzalacetone;4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one;4-Hydroxy-3-methoxybenzylideneacetone; 4-Hydroxy-3-methoxystyryl methyl ketone;Dehydro[0]-paradol; Dehydrogingerone; Dehydrozingerone; Feruloylmethane; NSC26613; NSC 4019; NSC 44708; NSC 45411; NSC 5316; Vanillalacetone; [0]-Paradol,dehydro-

Chemical Property of 4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE

Chemical Property:

• Vapor Pressure: 2.55E-05mmHg at 25°C
• Melting Point: 125-130oC
• Refractive Index: 1.4600 (estimate)
• Boiling Point: 348.2oC at 760 mmHg
• PKA: 9.94±0.31(Predicted)
• Flash Point: 136.9oC
• PSA: 46.53000
• Density: 1.154g/cm3
• LogP: 2.00300
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

98% ^*data from raw suppliers

4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C=CC1=CC(=C(C=C1)O)OC
• Description: Dehydrozingerone (1080-12-2) is a structural half analog of curcumin (Cat.# 10-1243) and is isolated from ginger rhizomes. Dehydrozingerone displays antioxidant, antibacterial and antifungal properties.1 It has also been shown to possess various antitumor effects2,3 and inhibit growth factor/peroxide-stimulated vascular smooth muscle function4.
• Uses: Vanillylidenacetone is one of ferulic acid derivatives. Studies have shown that vanillyl acetone has a certain inhibitory effect on Amaranthus, barnyardgrass, matang, dogwood and rape, among which the best inhibitory effect is on rape and Amaranthus.

Technology Process of 4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE

There total 41 articles about 4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

vanillin (121-33-5,8014-42-4) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one (1080-12-2,22214-42-2)

Guidance literature:

In water; at 90 ℃; for 0.5h; Green chemistry;

DOI:10.3390/molecules23092199

Reference yield: 95.0%

4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5) → (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one (1080-12-2,22214-42-2)

Guidance literature:

With oxygen; palladium diacetate; trifluoroacetic acid; In dimethyl sulfoxide; at 80 ℃; for 9h; Sealed tube;

DOI:10.1002/adsc.201801058

Reference yield: 94.0%

(E)-4'-((diisopropyl(2-methoxy-4-(3-oxobut-1-en-1-yl)phenoxy)silyl)methyl)-[1,1'-biphenyl]-2-carbonitrile → (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one (1080-12-2,22214-42-2)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1002/anie.201601999

upstream raw materials:

vanillin

acetone

1-triphenylphosphoranylidene-2-propanone

4-(4-((tert-butyldimethylsiloxy)-methyl)-3-methoxyphenyl)-but-3-ene-2-one

Downstream raw materials:

1t-(4-hydroxy-3-methoxy-phenyl)-5-piperidino-pent-1-en-3-one; hydrochloride

bis(2-hydroxybenzylidene)acetone

(E)-4-(4-acetyloxy, 3-methoxy phenyl)-3-buten-2-one

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

Refernces

• 1、 Tatsuzaki, Jin,Taniguchi, Masahiko,Bastow, Kenneth F.,Nakagawa-Goto, Kyoko,Morris-Natschke, Susan L.,Itokawa, Hideji,Baba, Kimiye,Lee, Kuo-Hsiung. "Anti-tumor agents 255: Novel glycyrrhetinic acid-dehydrozingerone conjugates as cytotoxic agents". . p. 6193 - 6199. Retrieved 2007.
• 2、 Elias,Rao. "Synthesis and anti-inflammatory activity of substituted (E)-4-phenyl-3-buten-2-ones". . p. 379 - 380. Retrieved 1988.
• 3、 Prabawati, Susy Yunita,Iskandar, Damayanti,Suci, Liimroati Purwo. "The synthesis and evaluation of vanillin derivatives as the fruit fly attractant". . p. 2197 - 2202. Retrieved 2018.
• 4、 Du, Yu-Ting,Zheng, Ya-Long,Ji, Yuan,Dai, Fang,Hu, Yong-Jing,Zhou, Bo. "Applying an Electrophilicity-Based Strategy to Develop a Novel Nrf2 Activator Inspired from Dietary [6]-Shogaol". . p. 7983 - 7994. Retrieved 2018.
• 5、 Theppawong, Atiruj,Van de Walle, Tim,Van Hecke, Kristof,Grootaert, Charlotte,Van Camp, John,D'hooghe, Matthias. "Synthesis of 1,4-Thiazepane-Based Curcuminoids with Promising Anticancer Activity". . p. 12583 - 12600. Retrieved 2019.
• 6、 Hafez, Taghrid S.,Henary, Maged M.,Mahran, Mohamed Refat H.. "Organophosphorus chemistry 32. 1 The reaction of vanillin, ortho-vanillin and piperonal with stabilized methylenetriphenylphosphoranes (wittig reagents)". . p. 33 - 44. Retrieved 1998.
• 7、 Moorkoth, Sudheer,Prathyusha, N. Sai,Manandhar, Suman,Xue, Yuanxin,Sankhe, Runali,Pai,Kumar, Nitesh. "Antidepressant-like effect of dehydrozingerone from Zingiber officinale by elevating monoamines in brain: in silico and in vivo studies". . p. 1273 - 1286. Retrieved 2021.
• 8、 Insuasty, Daniel,García, Stephanie,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Borosky, Gabriela L.,Laali, Kenneth K.. "Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents". . . Retrieved 2021.
• 9、 Pan, Gao-Fei,Zhu, Xue-Qing,Guo, Rui-Li,Gao, Ya-Ru,Wang, Yong-Qiang. "Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes". . p. 4774 - 4783. Retrieved 2018.
• 10、 Wenskowsky, Lea,Wagner, Michael,Reusch, Johannes,Schreuder, Herman,Matter, Hans,Opatz, Till,Petry, Stefan Matthias. "Resolving Binding Events on the Multifunctional Human Serum Albumin". . p. 738 - 743. Retrieved 2020.