胡椒醛 | 120-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 胡椒醛
• 中文别名: 3,4-亚甲二氧基苯甲醛；3,4-亚甲基二氧苯甲醛；洋茉莉醛
• 英文名称: piperonal
• 英文别名: 1,3-benzodioxole-5-carbaldehyde；benzo[d][1,3]dioxole-5-carbaldehyde；3,4-methylenedioxybenzaldehyde；heliotropin；1,3-benzodioxole-5-carboxaldehyde；benzo[d][1,3]dioxol-5-carbaldehyde；benzo[1,3]dioxole-5-carbaldehyde；piperonyl aldehyde
• CAS: 120-57-0
• 化学式: C₈H₆O₃
• 分子量: 150.134
• InChiKey: SATCULPHIDQDRE-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  在夏季气温较高时贮藏，或在日光照射下容易变色。常温下，在稀酸或碱溶液中则较为稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

代谢路径：胡椒醛转化为胡椒醇，然后被代谢成葡萄糖苷结合物。/来自表格/

Paths of metabolism: piperonal converted to piperonyl alcohol which is metabolized to glucoside conjugate. /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在家蝇中，胡椒醛被代谢为胡椒酸，后者可以转化为甘氨酸缀合物，或者转化为丙氨酸缀合物或谷氨酰胺缀合物。丙氨酸缀合物进一步转化为丝氨酸缀合物，而谷氨酰胺缀合物转化为谷氨酸缀合物。/来自表格/

In houseflies piperonal is metabolized to piperonylic acid which can be converted to a glycine conjugate or to an alanine conjugate or a glutamine conjugate. The alanine conjugate is further converted to a serine conjugate and the glutamine conjugate to a glutamate conjugate. /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中，胡椒醛被代谢成胡椒酸，然后转化为葡萄糖醛酸苷或甘氨酸结合物。

In rats piperonal is metabolized to piperonylic acid which is converted to glucuronide or to a glycine conjugate. /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

胡椒醇的β-葡萄糖苷在向家蝇注射胡椒醛后也被发现了。

The beta-glucoside of piperonyl alcohol has also been found after injection of...piperonal into houseflies.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

鉴定和使用：胡椒醛是一种固体。它用于香水、调味品和有机合成。是香草和樱桃风味的成分。它也被用于治疗头虱。人体研究：一个人摄入了十克胡椒醛，没有出现任何不良反应。动物研究：当大鼠口服13-115毫克胡椒醛5-9天时，观察到肝实质细胞脂肪浸润。每天通过胃管给予3只雄性和3只雌性大鼠900毫克/千克体重，持续4天，部分动物出现轻微的肝脏损伤。两组各20只雄性和20只雌性大鼠在含有0、0.1和0.5%胡椒醛的饮食中喂养2年，没有出现任何特定的不良反应。根据大鼠在500毫克/千克体重/天的剂量下喂养15周的研究，确定了NOAEL（无观察到不良反应水平）为500毫克/千克体重/天。胡椒醛在大肠杆菌DNA修复试验（Rec assay）中呈阳性，但未进行代谢激活，而在 Ames沙门氏菌回复突变试验或大肠杆菌WP2 uvrA回复突变试验中呈阴性。

IDENTIFICATION AND USE: Piperonal is a solid. It is used in perfumery, flavors, and organic syntheses. A constituent of vanilla and cherry flavors. It has also been used for the treatment of head lice. HUMAN STUDIES: Ten grams of piperonal were ingested by man without any adverse effect. ANIMAL STUDIES: When rats were given 13-115 mg piperonal perorally for 5-9 days, fatty infiltration of the liver parenchymal cells was noted. Intragastric administration of 900 mg/kg bw per day to 3 male and 3 female rats for 4 days produced slight gross liver damage in some animals. Groups of 20 male and 20 female rats were fed on diets containing 0, 0.1 and 0.5 % piperonal for 2 years without any specific adverse effect. Based of a feeding study in rats at 500 mg/kg bw per day for a period of 15 weeks NOAEL of 500 mg/kg bw was determined. Piperonal was positive in the Bacillus subtilis DNA-repair test (Rec assay) without metabolic activation, but it was negative when tested in the Ames Salmonella reversion assay or in the Escherichia coli WP2 uvrA reversion test.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

范围：胡椒醛是一种在香草中发现的芳香化合物，具有类似香草醛的花香。本研究旨在测试胡椒醛是否减轻高脂饮食（HFD）诱导的小鼠内脏脂肪积聚，并探讨其潜在的分子机制。 方法与结果：雄性C57BL/6N小鼠被喂食正常饮食、高脂饮食或添加了0.05%胡椒醛的高脂饮食（PSD）10周。与高脂饮食组相比，PSD饮食组的小鼠体重增加、总内脏脂肪垫重量和血浆脂质水平均有所减轻。胡椒醛补充高脂饮食增加了小鼠白色脂肪组织（WAT）中某些腺苷酸环化酶（Adcy）同型和蛋白激酶A（PKA）的mRNA表达。与高脂饮食组相比，PSD饮食组小鼠的脂肪生成相关基因下调，而脂肪酸氧化和产热相关基因上调。胡椒醛通过减少其底物（ATP）的Km值，直接激活小鼠WAT准备的血浆膜中的Adcy。此外，胡椒醛在3T3-L1细胞中诱导的抑制脂肪细胞分化和提高Adcy和PKA活性的作用被Adcy抑制剂消除。 结论：胡椒醛在高脂饮食喂养的小鼠中的抗脂肪生成作用似乎与WAT中增加的Adcy-PKA信号传导有关。

SCOPE: Piperonal is an aromatic compound found in vanilla and has a floral odor resembling vanillin. This study was aimed to test whether piperonal attenuates visceral adiposity induced by a high-fat diet (HFD) in mice and to explore the underlying molecular mechanisms. METHODS AND RESULTS: Male C57BL/6N mice were fed a normal diet, HFD, or 0.05% piperonal-supplemented HFD (PSD) for 10 weeks. PSD-fed mice showed attenuation of body weight gain, total visceral fat pad weights, and plasma lipid levels compared to HFD-fed mice. Piperonal supplementation of the HFD increased the mRNA expression of certain isotypes of adenylate cyclase (Adcy) and protein kinase A (PKA) in the white adipose tissue (WAT) of mice. The adipogenesis-related genes were downregulated, whereas fatty acid oxidation- and thermogenesis-related genes were upregulated in the WAT of PSD-fed mice compared to those in HFD-fed mice. Piperonal directly activated Adcy by decreasing the Km for its substrate (ATP) in plasma membranes prepared from the WAT of mice. Furthermore, piperonal-induced inhibition of adipocyte differentiation and elevation of Adcy and PKA activities in 3T3-L1 cells were abrogated by an Adcy inhibitor. CONCLUSION: The anti-adipogenic effect of piperonal in mice fed the high-fat diet appears to be associated with increased Adcy-PKA signaling in WAT.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或小型气囊，按培训操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者发生呕吐，让患者身体前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止误吸。保持患者安静，维持正常体温。寻求医疗帮助。/毒药A和B/

Immediate First Aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket musk, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. if vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要进行治疗……。监测休克，如有必要进行治疗……。预见并处理癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

1. 以黄樟油素为原料可制取洋茉莉醛。在10份酒精中加入6份氢氧化钾，投入异构化反应釜中。搅拌并加热至回流使氢氧化钾溶解。然后在此溶液中加入6份纯黄樟油素，缓缓加热混合物使之回流，反应15～20小时。反应完毕后冷却混合物，再用水稀释，然后蒸去大部分酒精。余下的粗异黄樟油素用真空分馏的方法除去其中杂质。

在搪玻璃反应釜中，先投入26份蒸馏水、11.6份重铬酸钠和少量对氨基苯碘酸，搅拌溶解。加入6.6份异黄樟油素，在室温下搅拌混合后，一边搅拌一边缓缓加入98%的工业用硫酸。因反应放热需在夹套中通冷水冷却，并要求加硫酸的速度缓慢。硫酸加完后继续反应0.5小时后静置分层。分出苯层，余下的酸性混合物再在40℃下用8份苯再萃取一次。合并二次萃取的苯液，洗涤并中和，再将苯蒸出（回收）。蒸馏釜中留下的粗制洋茉莉醛再进行真空分馏即得半固态的洋茉莉醛。将它溶于等量95%酒精中微热使洋茉莉醛完全溶解，加适量活性炭搅拌0.5小时后过滤、冷却结晶、低温干燥，可得到纯度较高的洋茉莉醛。

2. 烟草中的洋茉莉醛可以采用BU 14标准。合成制备方法有两种：半合成法和全合成法。半合成法是以天然黄樟油中的黄樟油素为原料，在碱性条件下异构化成为异黄樟油素，再用臭氧氧化成为洋茉莉醛；全合成法则以邻苯二酚和乙醛酸为原料进行合成。