358748-29-5

Basic information

• Product Name: 2-O-Acetylzeylenone
• Synonyms: 2-O-Acetylzeylenone;(4R,5S,6S)-5-(Acetyloxy)-4-(benzoyloxy)-6-[(benzoyloxy)methyl]-6-hydroxy-2-cyclohexen-1-one
• CAS NO: 358748-29-5
• Molecular Formula: C23H20O8
• Molecular Weight: 424.4001
• Mol File: 358748-29-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-O-Acetylzeylenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-O-Acetylzeylenone(358748-29-5)
• EPA Substance Registry System: 2-O-Acetylzeylenone(358748-29-5)

Safety Data

• Hazardous Substances Data: 358748-29-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-O-Acetylzeylenone is used as an anti-inflammatory agent for its ability to inhibit nitric oxide production, which is involved in inflammation. This makes it a potential therapeutic agent for conditions characterized by inflammatory processes.
Used in Nutraceutical Industry:
2-O-Acetylzeylenone is used as a natural source of nutraceuticals due to its antioxidant properties and potential health benefits. Its strong free radical scavenging activity suggests that it could be incorporated into dietary supplements or functional foods to support overall health and well-being.
Used in Antioxidant Applications:
2-O-Acetylzeylenone is used as an antioxidant agent for its demonstrated free radical scavenging activity. This property makes it a promising candidate for the development of treatments for conditions involving oxidative stress, such as neurodegenerative diseases and aging-related disorders.
Used in Research and Development:
2-O-Acetylzeylenone is used as a subject of research and development in the field of natural medicine. Its pharmacological properties and potential applications in various therapeutic areas make it an interesting compound for further exploration and potential commercialization.

Upstream product

• 697266-01-6 (1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-benzoyloxy-cyclohex-4-en-6-one 
• 98-88-4 benzoyl chloride 
• 77-95-2 (1R,3R,4R,5R)-(-)-quinic acid 
• 75-36-5 acetyl chloride 
• 193410-84-3 (-)-Tonkinenin A 
• 78804-17-8 ((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure–activity relationship of its derivatives

Natural products–polyoxygenated cyclohexenes exhibited potent anti-tumor activity, such as zeylenone, which is a natural product isolated from Uvaria grandiflora Roxb. This article will attempt to establish a gram-scale synthesis method of (+)-zeylenone and explain the structure–activity relationship of this kind of compound. Total synthesis of (+)-zeylenone was completed in 13 steps with quinic acid as the starting material in 9.8% overall yield. The highlight of the route was the control of the three carbon's chirality by single step dihydroxylation. In addition, different kinds of derivatives were designed and synthesized. Cell Counting Kit-8 (CCK8) assay was used for evaluating antitumor activity against three human cancer cell lines. The structure–activity relationship suggested that compounds with both absolute configurations exhibited tumor-suppressive effects. Moreover, hydroxyls at the C-1/C-2 position were crucial to the activity, and the esterification of large groups at C-1 hydroxyl eliminated the activity. Hydroxyl at the C-3 position was also important as proper ester substituent could increase the potency.

Zeylenone derivative as well as preparation method and application thereof

The invention provides a zeylenone derivative as well as a preparation method and application thereof. The zeylenone derivative comprises a first derivative of a (-)-zeylenone configuration and a second derivative of a (+)-zeylenone configuration, wherein the first derivative has a structure as shown in a formula (II), a formula (III) or a formula (IV); and the second derivative has a structure asshown in a formula (V), a formula (VI), a formula (VII), a formula (VIII), a formula (IX) or a formula (X). The zeylenone derivative with the specific structure has better antitumor activity, has great influence on IC50 values of malignant melanoma, human liver cancer, human neuroblastoma and dog breast tumor, and can enable the IC50 value to be a very small value. The zeylenone derivative can beused for preparing anti-malignant melanoma drugs, anti-human liver cancer drugs, anti-human neuroblastoma drugs and anti-dog breast tumor drugs.

Four polyoxygenated cyclohexenes from the Chinese tree, Uvaria purpurea.

Two novel polyoxygenated cyclohexenes, 6-methoxyzeylenol (3) and 2-acetoxyzeylenone (4), together with two known compounds, zeylenol (1) and zeylenone (2), were isolated from the heartwood of the Chinese tree, Uvaria purpurea. Zeylenol (1) and zeylenone (