78954-23-1

Basic information

• Product Name: yakuchinone-A
• Synonyms: yakuchinone-A;1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone
• CAS NO: 78954-23-1
• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.40276
• Mol File: 78954-23-1.mol

Chemical Properties

• Boiling Point: 495.8°C at 760 mmHg
• Flash Point: 174.3°C
• Appearance: /
• Density: 1.095g/cm³
• Vapor Pressure: 1.87E-10mmHg at 25°C
• Refractive Index: 1.559
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: yakuchinone-A(CAS DataBase Reference)
• NIST Chemistry Reference: yakuchinone-A(78954-23-1)
• EPA Substance Registry System: yakuchinone-A(78954-23-1)

Safety Data

• Hazardous Substances Data: 78954-23-1(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Yakuchinone-A is used as an antineoplastic agent for its ability to inhibit the growth and proliferation of cancer cells. It has shown potential in targeting various types of cancer, including solid malignancies, by interfering with the signaling pathways that promote cancer cell survival and proliferation.
Used in Anti-inflammatory Applications:
Yakuchinone-A is used as an anti-inflammatory agent due to its inhibitory activities against COX-1 and COX-2 enzymes. These enzymes are responsible for the production of prostaglandins, which are involved in the inflammation process. By inhibiting these enzymes, yakuchinone-A can help reduce inflammation and alleviate pain associated with various conditions.
Used in NO Synthase Inhibition:
Yakuchinone-A is used as an inhibitor of NO synthase, an enzyme involved in the production of nitric oxide (NO). Nitric oxide is a molecule that plays a role in various physiological processes, including blood vessel dilation and immune response. However, excessive production of NO can lead to inflammation and other harmful effects. By inhibiting NO synthase, yakuchinone-A can help regulate nitric oxide levels and potentially reduce inflammation and related issues.

InChI:InChI=1/C20H24O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,12,14-15,22H,5-6,9-11,13H2,1H3

Upstream product

• 121-33-5 vanillin 
• 3360-41-6 4-phenyl-butan-1-ol 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 4173-44-8 6-phenylhexa-3,5-dien-2-one 
• 14371-10-9 (E)-3-phenylpropenal 
• 14171-89-2 1-phenyl-5-hexanone 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 290820-47-2 (2E)-3-[4-[[tert-butyldimethylsilyl]oxy]-3-methoxyphenyl]acrylaldehyde 
• 458-36-6 trans-coniferyl aldehyde 
• 335594-14-4 1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-7-phenyl-hept-1-en-3-ol 
• 335594-16-6 1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-7-phenyl-hept-1-en-3-one 
• 873376-14-8 1-benzoyloxy-4-chloromethyl-2-methoxy-benzene 
• 81840-57-5 1-(3-methoxy-4-hydroxyphenyl)-7-phenylhept-1-en-3-one 

Relevant articles and documents

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

A concise and efficient method for the large-scale total synthesis of oxyphyllacinol (1) has been achieved in six steps with an overall yield of 46%. Simultaneously, yakuchione-A (11) was obtained in a satisfactory yield (52%) during the process. By employing a Weinreb amide (6) as the key masonry block, yakuchione-B (13) was also constructed in a great overall yield (56%) and high purity. To overcome the challenges regarding the practical scale, high purity, and reproducibility, the synthetic route that was processed takes advantage of available materials, conventional reactions, and convenient purification methods without using column chromatography.

Synthesis method of yakuchinone-A

The invention provides a synthesis method of yakuchinone-A, and belongs to the technical field of organic chemical synthesis. The preparation method is suitable for industrial production of the yakuchinone-A. According to the method, vanillin is taken as a starting raw material, an alkylation reaction, a wittig-harner reaction, a hydrolysis reaction, a reduction reaction and various reactions are sequentially carried out to finally obtain crude yakuchinone, and then the crude yakuchinone is recrystallized by an organic solvent to prepare the high-purity yakuchinone. The method specifically characterized by synthesizing a compound 8 through the vanillin, synthesizing a compound 9 through the compound 8, synthesizing a compound 10 through the compound 9, synthesizing a compound 11 through the compound 10, and finally synthesizing the yakuchinone-A through the compound 11, and then obtaining the high-purity yakuchinone-A through a recrystallization means. The synthesis method disclosed by the invention has the advantages of easily available raw materials, low cost, easiness in operation, good safety, less pollution, simplicity in purification, easiness in quality control and the like.

Suppression of inducible nitric oxide synthase expression by yakuchinones and their analogues

Analogues of yakuchinones were synthesized as inhibitors of nitric oxide production in lipopolysaccharideactivated macrophage cell line, RAW 264.7 cells. We prepared stronger inhibitors than the original natural molecules, yakuchinones A and B reported from Alpinia oxyphylla. From the limited structural activity relation study of analogues, we concluded that the optimal length of linker between two aryl groups and the presence of enone moiety in the linker were identified as essential for the activity. The IC50 value of the most potent structure was 0.92 μM. The active analogues suppressed the expression of inducible nitric oxide synthase protein and mRNA.

Selective Reduction of α,β-Unsaturated Carbonyl Compounds with Carbon Monoxide and Water Assisted by Seleniium

Carbon-carbon double bond of α,β-unsaturated carbonyl compounds can be reduced selectively with hydrogen selenide, generated in situ by the reaction of elemental selenium with carbon monoxide and water in the presence of strongly basic tertiary amine.

Synthesis of diarylheptanoids and assessment of their pungency

With the aim of correlating pungency with substituent groups on one benzene ring, various analogues of yakuchinones were synthesized by means of the Claisen-Schmidt reaction. Their pungencies were assessed by direct comparison of the threshold concentrations obtained in taste experiments. The presence of a phenolic hydroxyl group was indispensable for high pungency, while that of a 1,2-double bond of the heptanone part tended to decrease the pungency.