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4-Acetoxy-3,5-dimethoxybenzaldehyde is an organic compound that belongs to the benzaldehyde family. It is a white solid with chemical properties that make it suitable for use in the synthesis of various pharmaceutical drugs and research chemicals. Its potential psychoactive effects and association with recreational drug use highlight the need for further research into its pharmacological properties and potential uses.

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  • 53669-33-3 Structure
  • Basic information

    1. Product Name: 4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE
    2. Synonyms: ACETYL SYRINGALDEHYDE;AKOS BBS-00003176;4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE;4-ACETYL SYRINGALDEHYDE;4-FORMYL-2,6-DIMETHOXYPHENYL ACETATE;O-Acetylsyringaldehyde;4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE 98%;3,5-Dimethoxy-4-acetoxybenzaldehyde
    3. CAS NO:53669-33-3
    4. Molecular Formula: C11H12O5
    5. Molecular Weight: 224.21
    6. EINECS: N/A
    7. Product Categories: Aromatic Aldehydes & Derivatives (substituted)
    8. Mol File: 53669-33-3.mol
  • Chemical Properties

    1. Melting Point: 115-117 °C(lit.)
    2. Boiling Point: 307.9 °C at 760 mmHg
    3. Flash Point: 152.3 °C
    4. Appearance: /
    5. Density: 1.2 g/cm3
    6. Vapor Pressure: 0.000705mmHg at 25°C
    7. Refractive Index: 1.53
    8. Storage Temp.: Refrigerator, under inert atmosphere
    9. Solubility: Acetonitrile (Slightly), Chloroform (Slightly),Methanol (Slightly)
    10. CAS DataBase Reference: 4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE(53669-33-3)
    12. EPA Substance Registry System: 4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE(53669-33-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 53669-33-3(Hazardous Substances Data)

53669-33-3 Usage

Uses

Used in Pharmaceutical Industry:
4-Acetoxy-3,5-dimethoxybenzaldehyde is used as an intermediate in the synthesis of various pharmaceutical drugs for its ability to contribute to the development of new medications.
Used in Research Chemicals:
4-ACETOXY-3,5-DIMETHOXYBENZALDEHYDE is used as a research chemical, facilitating the study and understanding of its chemical properties and potential applications in scientific research.
Used in the Synthesis of Hallucinogenic Substances:
Due to its chemical properties, 4-Acetoxy-3,5-dimethoxybenzaldehyde is used in the production of certain hallucinogenic substances, although its precise mechanism of action and effects on the human body are not fully understood.
Note: The use of 4-Acetoxy-3,5-dimethoxybenzaldehyde in the synthesis of hallucinogenic substances should be approached with caution due to its potential psychoactive effects and the need for further research into its safety and efficacy.

Check Digit Verification of cas no

The CAS Registry Mumber 53669-33-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,6,6 and 9 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 53669-33:
(7*5)+(6*3)+(5*6)+(4*6)+(3*9)+(2*3)+(1*3)=143
143 % 10 = 3
So 53669-33-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H12O5/c1-7(13)16-11-9(14-2)4-8(6-12)5-10(11)15-3/h4-6H,1-3H3

53669-33-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (4-formyl-2,6-dimethoxyphenyl) acetate

1.2 Other means of identification

Product number -
Other names O-acetylsyringaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:53669-33-3 SDS

53669-33-3Relevant articles and documents

Bioactive constitutents from the stems of Annona montana.

Wu,Chang,Ko,Teng

, p. 146 - 149 (1995)

Three structurally related acid amides, N-trans-feruloyltyramine (1), N-p-coumaroyltyramine (2), and N-trans-caffeoyltyramine (3), one lignan, (-)-syringaresinol (4), one aromatic aldehyde, syringaldehyde (5), and two steroids, beta-sitosterol and beta-si

Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min

, p. 2866 - 2874 (2021/11/12)

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.

Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

Guan, Li,Zhou, Junting,Lin, Qinghua,Zhu, Huilin,Liu, Wenyuan,Liu, Baolin,Zhang, Yanbo,Zhang, Jie,Gao, Jing,Feng, Feng,Qu, Wei

, p. 2657 - 2665 (2019/05/01)

Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 μM. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the α-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of ?7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

Investigating isomer specific photoprotection in a model plant sunscreen

Horbury,Flourat,Greenough,Allais,Stavros

supporting information, p. 936 - 939 (2018/02/07)

Sinapate esters are used throughout the plant kingdom, for example in photoprotection from ultraviolet radiation. Sinapate esters are naturally produced in their E-isomeric form; however, upon exposure to ultraviolet radiation, photoisomerization drives Z-isomer formation. To elucidate the photoprotection capacity of E vs. Z forms of sinapate esters, we explore the photochemistry of the model system, Z-ethyl sinapate. Following a novel Z-ethyl sinapate synthesis, we demonstrate that photoprotection is isomer independent. This suggests that, regarding photoprotection, there were no evolutionary pressures for biosynthesis of either isomer.

Halogen or nitrogen-containing group substituted bibenzyl analog, preparation method and uses thereof

-

Paragraph 0034; 0036; 0036; 0037; 0038; 0039, (2017/04/20)

The present invention discloses a halogen or nitrogen-containing group substituted bibenzyl analog or a pharmaceutically acceptable salt, a hydrate thereof, wherein the halogen or nitrogen-containing group substituted bibenzyl analog is represented by a f

Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis

Zhao, Xiaohong,Zhang, Yanjuan,Wei, Liping,Hu, Huayu,Huang, Zuqiang,Yang, Mei,Huang, Aimin,Wu, Juan,Feng, Zhenfei

, p. 52382 - 52390 (2017/11/27)

In order to learn about the esterification mechanism of lignin by mechanical activation-assisted solid-phase synthesis (MASPS) technology, lignin model compounds, p-hydroxy benzaldehyde (H), vanillin and vanillyl alcohol (G), and syringaldehyde (S), were used in the reaction with acetic anhydride, with 4-dimethyl amino pyridine (DMAP), sodium acetate, and sulfuric acid as catalysts. FTIR, NMR, and UV/vis analyses of the products showed that all of the catalysts could enhance the esterification. Both the phenolic hydroxyl and aliphatic hydroxyl participated in the esterification and the reactivity of the basic structural units of lignin had a descending order of H, G, and S. Oxidations could happen in the presence of unsaturated groups such as aldehyde in the lignin model compounds. The catalytic mechanism of the three kinds of catalyst was different, and the catalytic activity had a descending order of DMAP, sodium acetate, and sulfuric acid. The reactivity of phenolic hydroxyl was higher than that of aliphatic hydroxyl with DAMP as the catalyst, but the reactivity of aliphatic hydroxyl was higher than that of phenolic hydroxyl with sodium acetate or sulfuric acid as the catalyst. With sulfuric acid as the catalyst, some side reactions took place and resulted in the ring cleavage or cross-linking of the benzene ring. Consistency verification indicated that the use of lignin model compounds for studying the esterification mechanism of lignin was reasonable and feasible.

Synthesis and evaluation of neuroprotective 4-O-substituted chrysotoxine derivatives as potential multifunctional agents for the treatment of Alzheimer's disease

Guan, Li,Hao, Yanfeng,Chen, Lei,Wei, Meng-Lin,Jiang, Qin,Liu, Wen-Yuan,Zhang, Yan-Bo,Zhang, Jie,Feng, Feng,Qu, Wei

, p. 22827 - 22838 (2016/03/12)

A series of 4-O-substituted chrysotoxine (CTX) derivatives were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease (AD). In vitro assays indicated that four ring substituted compounds (2a, 2b, 3i and 3j)

A selective and mild glycosylation method of natural phenolic alcohols

Mastihubová, Mária,Poláková, Monika

, p. 524 - 530 (2016/04/08)

Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.

An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains

Li, Yan,Dai, Fang,Jin, Xiao-Ling,Ma, Meng-Meng,Wang, Yi-Hua,Ren, Xiao-Rong,Zhou, Bo

, p. 41 - 47 (2014/04/03)

To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2′-diphenyl-1-picrylhydrazyl (DPPH)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH --scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain.

Studies on the total synthesis of tenuifoliside B

Wu, Yongjiang,Shi, Qiyuan,Lei, Houliang,Liu, Xuesong,Luan, Lianjun

, p. 3757 - 3761 (2014/05/20)

An efficient synthesis of tenuifoliside B, which shows potential cognitive improvement and cerebral protective effects that may be further developed to become an anti-AD lead compound, has been developed starting from commercial available starting materials. Regioselective introductions of acyl groups to the OH-3′ and OH-6 of sucrose play the key steps by metal chelate-directed acylation and Mitsunobu esterification, respectively.

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