3,4-Dimethoxyphenol
(Synonyms: 3,4-二甲氧基苯酚) 目录号 : GC39327
3,4-Dimethoxyphenol 是植物来源的苯基丙烷化合物，可在化妆品中用作增白剂。3,4-Dimethoxyphenol 具有酪氨酸酶 (tyrosinase) 抑制活性。从细菌发酵液中分离出的 3,4-Dimethoxyphenol 具有有效的抗氧化作用。
Cas No.:2033-89-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >96.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,4-Dimethoxyphenol is a plant-derived phenylpropanoid compound and can use as a whitening agent in cosmetics. 3,4-Dimethoxyphenol has tyrosinase-inhibiting activity[1]. 3,4-Dimethoxyphenol has potent antioxidant effect isolated from the bacterial fermentation broth[2].
[1]. Tanimoto S, et al. Synthesis and cosmetic whitening effect of glycosides derived from several phenylpropanoids. Yakugaku Zasshi. 2006 Mar;126(3):173-7. [2]. Tomohiro Takaoa, et al. A Simple Screening Method for Antioxidants and Isolation of Several Antioxidants Produced by Marine Bacteria from Fish and Shellfish. Bioscience, Biotechnology, and Biochemistry. 1994, 58(10), 1780-1783.
| Cas No. | 2033-89-8 | SDF | |
| 别名 | 3,4-二甲氧基苯酚 | ||
| Canonical SMILES | OC1=CC=C(OC)C(OC)=C1 | ||
| 分子式 | C8H10O3 | 分子量 | 154.16 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.4868 mL | 32.4338 mL | 64.8677 mL |
| 5 mM | 1.2974 mL | 6.4868 mL | 12.9735 mL |
| 10 mM | 0.6487 mL | 3.2434 mL | 6.4868 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
On the way to understand antioxidants: chromanol and dimethoxyphenols gas-phase acidities
J Mass Spectrom 2011 Jul;46(7):640-8.PMID:21671439DOI:10.1002/jms.1933.
Some antioxidant mechanisms displayed by several phenolic compounds relate with OH bond dissociation energy. One way for its determination, in the gas-phase, relies on acidity measurements. Gas-phase acidities were determined experimentally, applying the kinetic method, for chromanol and four dimethoxyphenols, and theoretically through quantum chemical DFT calculations for chromanol, six dimethoxyphenols and 3,4,5-trimethoxyphenol. The experimental acidity order, 2,3-dimethoxyphenol > 3,5-dimethoxyphenol > 2,6-dimethoxyphenol > 3,4-Dimethoxyphenol ≈ phenol > chromanol shows good agreement with the theoretical acidity order, 2,5-dimethoxyphenol > 2,3-dimethoxyphenol > 3,4,5-trimethoxyphenol > 3,5-dimethoxyphenol ≈ 2,4-dimethoxyphenol > 2,6-dimethoxyphenol > 3,4-Dimethoxyphenol > phenol > chromanol. These acidity trends were rationalized in terms of the substituent effects on the thermodynamic stabilities both of the parent phenols and the corresponding phenoxide ions. DFT calculations also evidenced the occurrence of intramolecular C-H···O hydrogen bonds whenever there are vicinal substituents (either OH, O(-) or OCH(3)) which induce further stabilization of the geometries.
Synthesis of 7,2'-Dihydroxy-4',5'-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity
Molecules 2022 Oct 7;27(19):6660.PMID:36235197DOI:10.3390/molecules27196660.
This paper reports a concise and scalable method for the synthesis of the phytoestrogen 7,2'-dihydroxy-4',5'-dimethoxyisoflavanone 1 via an optimized synthetic route. Compound 1 was readily obtained in 11 steps and 11% overall yield on a gram scale from commercially available 3,4-Dimethoxyphenol. The key features of the synthesis include the construction of the deoxybenzoin unit through a sequence of Claisen rearrangement, oxidative cleavage, and aryllithium addition and the efficient synthesis of the isoflavanone architecture from highly functionalized 2-hydroxyketone.
Sesquiterpenoid and phenolic glucoside gallates from Lagerstroemia balansae
Planta Med 2011 Nov;77(17):1944-6.PMID:21800279DOI:10.1055/s-0031-1280093.
Three new compounds, including a sesquiterpenoid glucoside gallate, 2 Z,4 E,1' R,2' S,4' R,6' S-dihydrophaseic acid 4'-O-(6''-O-galloyl)-β-D-glucopyranoside (1), two new phenolic glucoside gallates, 4-hydroxy-3,5-dimethoxybenzoic acid 4-O-(6'-O-galloyl)-β-D-glucopyranoside (2) and 3,4-Dimethoxyphenol 1-O-(6'-O-galloyl)-β-D-glucopyranoside (3), together with eight known compounds (4-11), have been isolated from the stems of Lagerstroemia balansae. Their structures were elucidated on the basis of chemical and spectroscopic evidences.
Synthesis and cosmetic whitening effect of glycosides derived from several phenylpropanoids
Yakugaku Zasshi 2006 Mar;126(3):173-7.PMID:16508241DOI:10.1248/yakushi.126.173.
Plant-derived phenylpropanoid compounds (4-ethyl-2-methoxyphenol, 2,6-dimethoxyphenol, 2,3-dimethoxyphenol, 3,4-Dimethoxyphenol, 3,5-dimethoxyphenol, 3,4-dihydroxycinnamic acid, 4-hydroxy-3-methoxycinnamic acid, and 3-hydroxy-4-methoxycinnamic acid) were glycosidated to form glycoside compounds. We evaluated the effects of these compounds on the inhibition of tyrosinase and melanin synthesis and their cytotoxicity from the viewpoint of their use as whitening agents in cosmetics. Some compounds had more potent tyrosinase-inhibiting activity than commercial arbutin, which was used as a control, and showed no cytotoxicity at low concentration ranges.
Constituents from the bark of Tabebuia impetiginosa
Phytochemistry 2004 Jul;65(13):2003-11.PMID:15280007DOI:10.1016/j.phytochem.2004.06.012.
The bark of Tabebuia impetiginosa afforded nineteen glycosides, consisting of four iridoid glycosides, two lignan glycosides, two isocoumarin glycosides, three phenylethanoid glycosides and eight phenolic glycosides. Their structures were determined using both spectroscopic and chemical methods. Iridoid glycosides, phenylethanoid glycosides and lignan glycosides had ajugol, osmanthuside H and secoisolariciresinol 4-O-beta-D-glucopyranoside as their structural elements, respectively, whereas the aglycone moieties of the isocoumarin glycosides were considered to be (-)-6-hydroxymellein. Phenolic glycosides had 4-methoxyphenol, 2,4-dimethoxyphenol, 3,4-Dimethoxyphenol, 3,4,5-trimethoxyphenol and vanillyl 4-hydroxybenzoate as each aglycone moiety. Additionally, the sugar chains of these isocoumarin glycosides and phenolic glycosides were concluded to be beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside as well as those of osmanthuside H and above phenylethanoid glycosides.