Diallyl phthalate   中文名称: 1,2-苯二甲酸二烯丙酯

Absorption, Distribution and Excretion
Thirty minutes after rats and mice were treated orally with (14)C-labeled diallyl phthalate (DAP), the highest levels of radioactivity were found in small intestine, liver, dermis, muscles, blood, and kidneys. After 24 hr, about 6-7% of the radioactivity was present in rats and 1-3% in mice. In rats, 60% of the radioactivity was found in urine and 30% was exhaled as CO2. In mice, 91% was present in urine, and only 8% was detected as CO2.

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Metabolism / Metabolites
Fischer 344 rats and B6C3F1 mice were given 14(C) diallyl phthalate, 1, 10, or 100 mg/kg po or 10 mg/kg iv, and placed in metabolism cages for 24 hr. In rats, 25-30% of the diallyl phthalate was excreted as carbon dioxide, and 50-70% appeared in the urine within 24 hr. In mice, 6-12% of the diallyl phthalate was excreted as carbon dioxide, and 80-90% was excreted in the urine within 24 hr. Monoallyl phthalate (MAP), allyl alcohol, 3-hydroxypropylmercapturic acid (HPMA), and an unidentified polar metabolite (PM) were found in the urine of rats and mice dosed with diallyl phthalate. The polar metabolite was present in the urine of rats dosed with diallyl phthalate or allyl alcohol, indicating that the compound is a metabolite of allyl alcohol. There was no difference between the species in the quantity of allyl alcohol excreted, but mice excreted more monoallyl phthalate (39 vs 33%), 3-hydroxypropylmercapturic acid (28 vs 17%), and polar metabolite (20 vs 8%) than rats.
The following metabolic pathway is suggested for diallyl phthalate (DAP). First, the diester is hydrolyzed to monoallyl phthalate (MAP) and allyl alcohol (AA). AA can be oxidized to acrolein and acrylic acid and further metabolized to CO2. Allyl alcohol and acrolein can also react with reduced glutathione to form 3-hydroxypropylmercapturic acid. Alternatively, allyl alcohol and acrolein can be oxidized to the epoxides glycidol and glycidaldehyde. These epoxides can be hydrolyzed to glycerin and glyceraldehyde or conjugated with reduced glutathione. It is not clear whether DAP is metabolized by this pathway in vivo. However, some of the products of the aforementioned reactions (e.g., monoallyl phthalate, 3-hydroxypropylmercapturic acid, allyl alcohol) as well as an unidentified polar metabolite have been detected in urine of rats and mice treated with DAP.
... Diallyl phthalate (DAP) is more hepatotoxic to rats than to mice, and demonstrated the same species difference in toxicity for allyl alcohol (AA). The data suggest that the toxicity of diallyl phthalate probably results from allyl alcohol cleaved from diallyl phthalate. To determine if the species difference in susceptibility to hepatotoxicity resulted from differences in the disposition and metabolism of diallyl phthalate, Fischer 344 rats and B6C3F1 mice were given 14(C) diallyl phthalate, 1, 10, or 100 mg/kg po or 10 mg/kg iv, and placed in metabolism cages for 24 hr. In rats, 25-30% of the diallyl phthalate was excreted as carbon dioxide, and 50-70% appeared in the urine within 24 hr. In mice, 6-12% of the diallyl phthalate was excreted as carbon dioxide, and 80-90% was excreted in the urine within 24 hr. Monoallyl phthalate (MAP), allyl alcohol, 3-hydroxypropylmercapturic acid (HPMA), and an unidentified polar metabolite (PM) were found in the urine of rats and mice dosed with diallyl phthalate. The polar metabolite was present in the urine of rats dosed with diallyl phthalate or allyl alcohol, indicating that the compound is a metabolite of allyl alcohol. There was no difference between the species in the quantity of allyl alcohol excreted, but mice excreted more monoallyl phthalate (39 vs 33%), 3-hydroxypropylmercapturic acid (28 vs 17%), and polar metabolite (20 vs 8%) than rats.
Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (A2884)

Toxicity Summary
Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (A2883)

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Toxicity Data
LC50 (rat) = 5,200 mg/m3/1h
LD50: 656 mg/kg (Oral, Rat) (T13)
LD50: 3.8-3.9 g/kg (Dermal, Rabbit) (T29)
LD50: 700 mg/kg (Intraperitoneal, Mouse) (A724)

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Non-Human Toxicity Values
LD50 Rat oral 656 mg/kg
LD50 Rabbit oral 1.7 g/kg /From table/
LD50 Rabbit dermal 3400 mg/kg /From table/
LD50 Mouse ip 700 mg/kg
For more Non-Human Toxicity Values (Complete) data for DIALLYL PHTHALATE (7 total), please visit the HSDB record page.

Diallyl phthalate is a clear pale-yellow liquid. Odorless. (NTP, 1992)
Diallyl phthalate is a phthalate ester. Phthalate esters are esters of phthalic acid and are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are hazardous due to their ability to act as endocrine disruptors. They are being phased out of many products in the United States and European Union due to these health concerns. (L1903)

C14H14O4

246.25856

246.089

131-17-9

8560

Nearly colorless, oily liquid

1.1±0.1 g/cm3

329.1±0.0 °C at 760 mmHg

-70 °C

164.8±20.7 °C

0.0±0.7 mmHg at 25°C

1.524

3.29

52.6

0

4

8

18

290

0

C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C

QUDWYFHPNIMBFC-UHFFFAOYSA-N

InChI=1S/C14H14O4/c1-3-9-17-13(15)11-7-5-6-8-12(11)14(16)18-10-4-2/h3-8H,1-2,9-10H2

bis(prop-2-enyl) benzene-1,2-dicarboxylate

Diallyl phthalate NSC-7667 NSC 7667 NSC7667

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

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注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

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注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

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口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

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口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

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注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。