52946-22-2

Usage

Uses

Used in Pharmaceutical Industry:
ACETOXYCHAVICOL ACETATE, D/L-1''is used as an anti-inflammatory agent for its ability to inhibit the NF-κB signaling pathway, which plays a crucial role in regulating inflammation.
Used in Anticancer Applications:
ACETOXYCHAVICOL ACETATE, D/L-1''is used as a potential anticancer agent due to its impact on intracellular signaling pathways, which may help in the development of novel cancer treatments.
Used in Antiviral Applications:
ACETOXYCHAVICOL ACETATE, D/L-1''is used as an antiviral agent for its ability to interfere with viral replication processes by targeting specific cellular pathways.
Used in Drug Delivery Systems:
ACETOXYCHAVICOL ACETATE, D/L-1''can be used in the development of drug delivery systems to enhance the bioavailability and therapeutic outcomes of various medications by leveraging its cellular effects on intracellular signaling pathways.

Upstream product

• 169436-30-0 4-((S)-1-Hydroxy-allyl)-phenol 
• 108-24-7 acetic anhydride 
• 53580-61-3 4-(1-hydroxy-2-propenyl)phenol 
• 52946-22-2 1-acetoxychavicol acetate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 387351-55-5 (S)-4-O-tert-butyldimethylsilyl-1'-hydroxychavicol 
• 194156-04-2 1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol 

Downstream Products

• 1160172-97-3 C₁₅H₁₉NO₄S 
• 113944-48-2 (E)-3-(4-acetoxyphenyl)-2-propenyl acetate 
• 129319-15-9 (+/-)-2',3'-dihydroacetoxychavicol acetate 
• 94723-93-0 acetic acid (E)-4-(3-hydroxypropenyl)phenyl ester 

Relevant academic research and scientific papers

Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit

An aqueous acetone extract from the fruit of Alpinia galanga (Zingiberaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50= 7.3 μg/mL). Through bioassay-guided separation of the extract, a new 7-O-9'-linked neolignan, named galanganol D diacetate (1), was isolated along with 16 known compounds including 14 phenylpropanoids (2–15). The structure of 1, including its absolute stereochemistry in the C-7 position, was elucidated by means of extensive NMR analysis and total synthesis. Among the isolates, 1 (IC50= 2.5 μM), 1'S-1'-acetoxychavicol acetate (2, 5.0 μM), and 1'S-1'-acetoxyeugenol acetate (3, 5.6 μM) exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1'-hydroxy moiety enhances the activity; and (iv) phenylpropanoid dimers with the 7-O-9'-linked neolignan skeleton exhibited higher activity than those with the corresponding monomer. Their respective enantiomers [1' (IC50= 1.9 μM) and 2' (4.5 μM)] and racemic mixtures [(±)-1 (2.2 μM) and (±)-2 (4.4 μM)] were found to exhibit melanogenesis inhibitory activities equivalent to those of the naturally occurring optical active compounds (1 and 2). Furthermore, the active compounds 1–3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity.

New Rev-export inhibitor from Alpinia galanga and structure-activity relationship

Bioassay-guided separation by use of the fission yeast expressing NES of Rev, an HIV-1 viral regulatory protein, disclosed 1′-acetoxychavicol acetate (ACA, 1) as a new inhibitor for nuclear export of Rev from the roots of Alpinia galanga. Both analysis for mechanism of action with biotinylated probe (2) and several synthesized analogs established crucial portions in 1 for Rev-export inhibitory activity.

Identification of dihydrogalangal acetate in galangal [Alpinia galangal (L.) Swartz] extracts

Dihydrogalangal acetate has been discovered for the first time in galangal roots [Alpinia galangal (L.) Swartz]. The compound has a taste sensation similar to galangal acetatesthe pungent principle of galangalsbut it is more stable in food and beverage applications. Therefore, dihydrogalangal acetate provides many advantages as a flavor ingredient for alcohol enhancement and taste modification. Dihydrogalangal acetate is present in approximately 0.0005% of fresh roots and in about 0.004% of dried roots. (S)-Dihydrogalangal acetate is found as the main optical isomer in galangal roots (98%), while its minor (R)-isomer is less abundant (2%). Enantiomers of galangal acetate and dihydrogalangal acetate were separated and evaluated by sensory analysis. (R)-Galangal acetate has a very faint woody and sweet aroma, and (R)-dihydrogalangal acetate is almost odorless, while (S)-galangal acetate has strong and (S)-dihydrogalangal acetate has weak pungent and woody notes. Although the aroma characters of these optical isomers are different, taste sensations were found to have no significant differences among galangal acetate, dihydrogalangal acetate, and their optical isomers.

Lipase-catalyzed preparation of optically active 1′-acetoxychavicol acetates and their structure-activity relationships in apoptotic activity against human leukemia HL-60 cells

Structure-activity relationships of 1′-acetoxychavicol acetate (ACA) for apoptotic activity against human leukemia HL-60 cells were investigated using optically active ACA and various racemic ACA analogues. Natural-type (or with different acyl group) ACA showed a high apoptotic activity, but the ortho or meta isomers, 4-deacetoxy analogue, and the 2′-3′ dehydrogenated derivative had no effect, or a weak activity. Optically active (R)- and (S)-ACA were prepared by a lipase-catalyzed esterification. Using a mixture of vinyl acetate-tetrahydrofuran (1:1 v/v) as a solvent at refluxing temperature, optically pure (R)- and (S)-ACA were obtained (99.7% ee and 99.1% ee, respectively). The apoptosis-inducing effects of both enantiomers were compared by means of an MTT assay and the detection of typical apoptotic phenomena (DNA fragmentation, caspase-3 activation, and PARP cleavage) and these two activities were almost equal. These results indicate that the essential moieties of ACA for apoptotic activity against HL-60 cells are both the presence of a 4-acetoxyl group and an unsaturated double bond between C-2′ and C-3′, and that the configuration at the 1′-position is unrelated to activity. All rights reserved.

Structure-activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

1′S-1′-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 μM. To clarify the structure-activity relationship of 1′S-1′- acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1′-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2′-3′ double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1′- and 2′-positions reduced the activity.

Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods

Cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.