3,5-Dimethoxyphenol
(Synonyms: 3,5-二甲氧基苯酚) 目录号 : GC60498
3,5-Dimethoxyphenol (Phloroglucinol dimethyl ether) is a toxin metabolite that can be found in human consuming yew (Taxus baccata) leaves.
Cas No.:500-99-2
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
3,5-Dimethoxyphenol (Phloroglucinol dimethyl ether) is a toxin metabolite that can be found in human consuming yew (Taxus baccata) leaves.
| Cas No. | 500-99-2 | SDF | |
| 别名 | 3,5-二甲氧基苯酚 | ||
| Canonical SMILES | OC1=CC(OC)=CC(OC)=C1 | ||
| 分子式 | C8H10O3 | 分子量 | 154.16 |
| 溶解度 | DMSO : 100 mg/mL (648.68 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| 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。
Monitoring of aglycons of yew glycosides (3,5-Dimethoxyphenol, myrtenol and 1-octen-3-ol) as first indicator of yew presence
Drug Test Anal 2013 Jun;5(6):474-9.PMID:22371422DOI:10.1002/dta.391.
The toxicity of yew (Taxus spp) is well known from ancient times and is mainly due to taxins acting as inhibitors of calcium and sodium transport across the cell membrane of cardiac myocytes. The confirmation of yew taxins in body fluids can be carried out by liquid chromatography-tandem mass spectrometry (LC-MS/MS). However, before selecting this precise but expensive technique, an orientation test should be done to ascertain yew presence as toxic agent in the organism. As the 3,5-Dimethoxyphenol (3,5-DMP), myrtenol and 1-octen-3-ol appear as glycosidically bound volatile compounds and are very yew specific, the detection of 3,5-DMP and the measurement of 1-octen-3-ol / myrtenol concentration ratio constitute reliable indicators of yew presence in forensic cases. The detection of these compounds is easily performed by gas chromatography-mass spectrometry (GC-MS) (SIM) after an enzymatic hydrolysis (β-glucosidase) allowing the release of volatile compounds from yew glycosides.
Unusual pseudosubstrate specificity of a novel 3,5-Dimethoxyphenol O-methyltransferase cloned from Ruta graveolens L
Arch Biochem Biophys 2005 Aug 1;440(1):54-64.PMID:16023070DOI:10.1016/j.abb.2005.05.026.
A cDNA was cloned from Ruta graveolens cells encoding a novel O-methyltransferase (OMT) with high similarity to orcinol or chavicol/eugenol OMTs, but containing a serine-rich N-terminus and a 13 amino acid insertion between motifs IV and V. Expression in Escherichia coli revealed S-adenosyl-l-methionine-dependent OMT activity with methoxylated phenols only with an apparent Km of 20.4 for the prime substrate 3,5-Dimethoxyphenol. The enzyme forms a homodimer of 84 kDa, and the activity was insignificantly affected by 2.0 mM Ca2+ or Mg2+, whereas Fe2+, Co2+, Zn2+, Cu2+ or Hg2+ were inhibitory (78-100%). Dithiothreitol (DTT) suppressed the OMT activity. This effect was examined further, and, in the presence of Zn2+ as a potential thiol methyltransferase (TMT) cofactor, the recombinant OMT methylated DTT to DTT-monomethylthioether. Sets of kinetic OMT experiments with 3,5-Dimethoxyphenol at various Zn2+/DTT concentrations revealed the competitive binding of DTT with an apparent Ki of 52.0 microM. Thus, the OMT exhibited TMT activity with almost equivalent affinity to the thiol pseudosubstrate which is structurally unrelated to methoxyphenols.
Fatal poisoning with Taxus baccata: quantification of paclitaxel (taxol A), 10-deacetyltaxol, baccatin III, 10-deacetylbaccatin III, cephalomannine (taxol B), and 3,5-Dimethoxyphenol in body fluids by liquid chromatography-tandem mass spectrometry
J Anal Toxicol 2012 Jan-Feb;36(1):36-43.PMID:22290751DOI:10.1093/jat/bkr012.
This method development was to confirm the fatal ingestion of toxic yew plant material in postmortem samples (stomach content, urine, femoral blood, cardiac blood, bile, and brain tissue) collected from a 22-year-old man who committed suicide by ingesting yew leaves. The analytical method was based on a liquid-liquid extraction under alkaline conditions followed by LC-MS-MS analysis. Chromatographic separation was achieved by HPLC on a Kinetex C18 2.6u (100 × 3 mm) coupled to a QTRAP 5500 system. The method allows the simultaneous identification and quantification of the yew alkaloids taxoids paclitaxel (taxol A), 10-deacetyltaxol, baccatin III, 10-deacetylbaccatin III, cephalomannine (taxol B), and 3,5-Dimethoxyphenol; the alkaloidal diterpenoids monoacetyltaxine, taxine B, monohydroxydiacetyltaxine, triacetyltaxine, and monohydroxytriacetyltaxine were also identified. The initial hypothesis of yew tree (Taxus baccata) poisoning was confirmed. The quantitative evaluation revealed taxoid concentrations ranging from 4.5 to 132 µg/L (stomach content), 1 to 200 µg/L (urine), <0.5 to 12 µg/L (cardiac blood), <0.5 to 7.3 µg/L (femoral blood), and 4.9 to 290 µg/L (bile). In brain tissue, none of these taxoids could be detected (<0.5 µg/L). In urine, after enzymatic hydrolysis, the concentration of 3,5-Dimethoxyphenol (3,5-DMP) was 23,000 µg/L. The alkaloidal diterpenoids were found in all postmortem samples. The newly developed LC-MS-MS method enables the identification of alkaloidal and non-alkaloidal diterpenoids and 3,5-Dimethoxyphenol in human body fluids and tissues for the confirmation of accidental or intentional poisonings with yew plant material.
Suicidal yew leave ingestion--phloroglucindimethylether (3,5-Dimethoxyphenol) as a marker for poisoning from Taxus baccata
Int J Legal Med 1993;106(1):45-50.PMID:8398891DOI:10.1007/BF01225024.
In a case of suicide in a depressive 19-year-old man with considerable ingestion of new leaves, resorption of yew ingredients could be demonstrated. The main substance could be identified as 3,5-Dimethoxyphenol, the aglycone of taxicatine, which is a typical ingredient of yew leaves. 3,5-Dimethoxyphenol was demonstrated in harvested yew leaves, stomach content and cardiac blood of the victim. Structure confirmation was achieved by means of HPLC, UV, GC-MS, IR and 1H-NMR spectroscopy. None of the Taxus alkoids could be identified. The components detected by TLC have not yet been identified. The results demonstrate that 3,5-Dimethoxyphenol can be used as a marker in cases of intoxication by yew ingredients.
Preliminary gas chromatography with mass spectrometry determination of 3,5-Dimethoxyphenol in biological specimens as evidence of taxus poisoning
J Anal Toxicol 2010 Jan-Feb;34(1):53-6.PMID:20109304DOI:10.1093/jat/34.1.53.
Taxus baccata is a widely distributed yew often associated with cases of fatal intoxication, which is related to the high amounts of cardiotoxic alkaloids, taxine A and taxine B, contained in its leaves. In this paper, a case of Taxus fatal poisoning, hypothesized by the forensic autopsy, has been confirmed by the application of both gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS-MS) techniques. A GC-MS method was used for the determination of the derivatized 3,5-Dimethoxyphenol, a cyanogenic aglylactone considered as a marker of Taxus poisoning, being present in all species of Taxus. The detection by LC-MS-MS of taxine B and isotaxine B in the biological specimens confirmed the absorption of cardiotoxic alkaloids and allowed to established the cause of death as the ingestion of Taxus baccata leaves.