植烷 | 638-36-8

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 植烷
• 中文别名: 2,6,10,14-四甲十六烷；1,1'-(1,1-二甲基-3-亚甲基-1,3-亚丙基)二苯
• 英文名称: phytane
• 英文别名: hexadecane, 2,6,10,14-tetramethyl-；2,6,10,14-tetramethyl hexadecane；2,6,10,14-tetramethyl-hexadecane；3,7,11,15-tetramethyl hexadecane；2,6,10,14-Tetramethylhexadecane；tetrahydroneophytadiene
• CAS: 638-36-8
• 化学式: C₂₀H₄₂
• 分子量: 282.553
• InChiKey: GGYKPYDKXLHNTI-UHFFFAOYSA-N

物化性质

• 沸点：
  69-71 °C0.001 mm Hg(lit.)
• 密度：
  0.791 g/mL at 20 °C(lit.)
• 溶解度：
  可溶于氯仿（少许）、己烷（少许）
• 颜色/状态：
  Clear, colorless liquid
• 蒸汽压力：
  3.3X10-3 mm Hg at 25 °C (est)
• 稳定性/保质期：

  存在于烟气中。

• 保留指数：
  1816;1811;1812;1814;1811;1814;1814;1815;1812;1816;1811;1812;1813

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

大鼠能够将2,6,10,14-四甲基十六烷（植烷）从肠道完整地吸收到淋巴中。体外实验表明，肠道微生物似乎无法代谢植烷。大鼠将植烷代谢为（a）一种三级醇，暂定为2,6,10,14-四甲基十六烷-2-醇，以及（b）多种短链酸，包括乙酸、异丁酸和2-甲基丁酸，这些酸通过尿液排出。即使在静脉注射植烷后，CO2也是一个非常少量的产物。在植烷降解过程中的类脂质中间体无法被检测到，这表明对分子的最初攻击是限速步骤。口服植烷后，尿液中会出现排泄产物，但静脉注射、腹腔注射或皮下给药后则不会。然而，无论是口服还是腹腔注射植烷，都会产生三级醇。

Rats absorb 2,6,10,14-tetramethylhexadecane (phytane) from the intestinal tract intact into the lymph. Intestinal microbes appeared to be unable to metabolize phytane in vitro. Rats metabolized phytane to (a) a tertiary alcohol tentatively identified as 2,6,10,14-tetramethylhexadecan-2-ol, and (b) a variety of short-chain acids which were excreted in the urine. These included acetic, isobutyric, and 2-methylbutyric acids. CO2 was a very minor product, even following intravenous injection of phytane. Lipoidal intermediates in the degradation of phytane could not be detected, suggesting that the initial attack on the molecule was rate-limiting. Urinary excretion products were apparent following oral but not intravenous, intraperitoneal, or subcutaneous administration of phytane. However, the tertiary alcohol was produced following both oral and intraperitoneal administration. ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

鉴定和使用：植烷是在25亿至30亿年前的岩石标本中发现的一种 hydrocarbon。知道仅由活体合成（是叶绿素的衍生物）并且能够承受热和压力，因此有助于确定地球上生命存在的时间（生物标记）。人类暴露和毒性：无数据。动物研究：大鼠从肠道吸收植烷，完整进入淋巴。

IDENTIFICATION AND USE: Phytane is a hydrocarbon found in rock specimens 2.5-3 billion years old. Know to be synthesized only by living organisms (is a derivative of chlorophyll) and to withstand heat and pressure, so helps to date the existence of life on earth (biomarker). HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: Rats absorbed phytane from the intestinal tract intact into the lymph.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练进行操作。如有必要，进行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者向前倾或将其置于左侧卧位（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。 /脂肪烃及其相关化合物/

/SRP:/ 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 mask, 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 the 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. /Aliphatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，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，并在必要时进行治疗……。预防并治疗癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于误食，如果患者能够吞咽、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。给予活性炭……。使用快速复温技术治疗冻伤……。/脂肪烃及其相关化合物/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Administer activated charcoal ... . Treat frostbite with rapid rewarming techniques ... ./Aliphatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊阀面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……监测心率和必要时治疗心律失常……开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……用地西泮（安定）或劳拉西泮（安定）治疗癫痫……使用丙美卡因氢氯化物协助眼部冲洗……/脂肪烃及其相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aliphatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

紧急和支援措施。1. 一般措施。为所有有症状的患者提供基本支持性护理。保持呼吸道通畅，必要时协助通气。给予补充氧气。监测动脉血气或血氧饱和度、胸部X光片、心电图，并将有症状的患者收入重症监护室。在有明显碳氢化合物中毒的患者中使用肾上腺素和其他β-肾上腺素能药物时要小心，因为可能会诱发心律失常。2. 肺吸入。观察4-6小时后仍然完全无症状的患者可以出院。相反，如果患者在到达时正在咳嗽，可能已经发生了吸入。如果出现支气管痉挛和低氧血症，给予补充氧气并进行治疗。不要使用类固醇或预防性抗生素。3. 吞咽。在绝大多数儿童意外吞咽的情况下，实际吞咽量少于5-10毫升，系统性中毒是罕见的。治疗主要是支持性的。注射。对于注射到指尖或手部的情况，尤其是涉及高压喷枪的情况，应立即咨询整形外科或手外科医生，因为通常需要迅速广泛地暴露、冲洗和清创。/碳氢化合物/

Emergency and supportive measures. 1. General. Provide basic supportive care for all symptomatic patients. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Monitor arterial blood gases or oximetry, chest radiographs, and ECG and admit symptomatic patients to an intensive care setting. Use epinephrine and other beta-adrenergic medications with caution in patients with significant hydrocarbon intoxication because arrhythmias may be induced. 2. Pulmonary aspiration. Patients who remain completely asymptomatic after 4-6 hours of observation may be discharged. In contrast, if the patient is coughing on arrival, aspiration probably has occurred. Administer supplemental oxygen and treat bronchospasm and hypoxia if they occur. Do not use steroids or prophylactic antibiotics. 3. Ingestion. In the vast majority of accidental childhood ingestions, less than 5-10 mL is actually swallowed and systemic toxicity is rare. Treatment is primarily supportive. Injection. For injections into the fingertip or hand, especially those involving a high-pressure paint gun, consult with a plastic or hand surgeon immediately, as prompt wide exposure, irrigation, and debridement are often required. /Hydrocarbons/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大鼠将2,6,10,14-四甲基十六烷（植烷）从肠道完整地吸收到淋巴中。肠道微生物在体外似乎无法代谢植烷。大鼠将植烷代谢为（a）一种三级醇，暂定为2,6,10,14-四甲基十六烷-2-醇，以及（b）多种短链酸，这些酸通过尿液排出。这些包括乙酸、异丁酸和2-甲基丁酸。即使在静脉注射植烷后，CO2也是一个非常少量的产物。在植烷降解中的脂质中间体无法被检测到，这表明对分子的初始攻击是限速步骤。口服植烷后可以观察到尿液排出产物，但在静脉内、腹腔内或皮下给药后则不明显。然而，无论是口服还是腹腔内给药，都会产生三级醇...

Rats absorb 2,6,10,14-tetramethylhexadecane (phytane) from the intestinal tract intact into the lymph. Intestinal microbes appeared to be unable to metabolize phytane in vitro. Rats metabolized phytane to (a) a tertiary alcohol tentatively identified as 2,6,10,14-tetramethylhexadecan-2-ol, and (b) a variety of short-chain acids which were excreted in the urine. These included acetic, isobutyric, and 2-methylbutyric acids. CO2 was a very minor product, even following intravenous injection of phytane. Lipoidal intermediates in the degradation of phytane could not be detected, suggesting that the initial attack on the molecule was rate-limiting. Urinary excretion products were apparent following oral but not intravenous, intraperitoneal, or subcutaneous administration of phytane. However, the tertiary alcohol was produced following both oral and intraperitoneal administration. ...

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2901100000
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  植烷 生成 2-甲基丁烷
  参考文献：
  名称：

  KISSIN, YURY V., IND. AND ENG. CHEM. RES., 26,(1987) N 8, 1633-1638

  摘要：

  DOI：
• 作为产物：
  描述：

  叶绿醇 生成 植烷
  参考文献：
  名称：

  Willstaetter; Mayer; Hueni, Justus Liebigs Annalen der Chemie, 1911, vol. 378, p. 114

  摘要：

  DOI：

文献信息

• Pyrolytic Formation of C₁₉Isoprenoid Hydrocarbons from Dihydrophytol: in Relation to the Genesis of Pristane in Petroleum
  作者：Mariko Ishiwatari、Keita Yamada、Ryoshi Ishiwatari

  DOI：10.1246/cl.2000.206

  日期：2000.3

  This study was concluded to elucidate a pathway for formation of C19 isoprenoid hydrocarbons (isops) in petroleum from chlorophylls. C19 isops are predominantly produced when dihydrophytol is heated at 320 °C for a period ranging from 1 to 5 h under vacuum while C20 isops are predominantly produced when chlorophyll a or phytol is heated. A radical chain reaction of decomposition of dihydrophytol is proposed as plausible pathway for producing C19 isops.

  这项研究旨在阐明石油中叶绿素形成 C19 异构烃（isops）的途径。在真空条件下，将双氢植物醇在 320 °C 下加热 1 至 5 小时，主要会产生 C19 异丙醇，而加热叶绿素 a 或植物醇，则主要会产生 C20 异丙醇。二氢植物醇分解的自由基链反应被认为是产生 C19 异构体的可能途径。
• The formation features of C10–C20 regular petroleum isoprenanes
  作者：G. N. Gordadze、M. V. Giruts、A. R. Poshibaeva、V. N. Koshelev

  DOI：10.1134/s0965544116080077

  日期：2016.8

  To model the formation processes of C-10-C-20 petroleum isoprenanes, thermolysis of regular and irregular C-20-C-40 isoprenanes (phytane, crocetane, squalane, and lycopane) and the suggested precursors of regular petroleum isoprenanes (phytol and isophytol) has been conducted. It has been shown that the thermolysis of these compounds results in the formation of regular, irregular, and pseudoregular isoprenanes; the trends in their distribution have been revealed; and the retention indices have been determined. It has been assumed that the pristane/phytane ratio, which is used in petroleum geochemistry, should be treated with caution.
• Soerensen; Soerensen, Acta Chemica Scandinavica (1947), 1949, vol. 3, p. 942
  作者：Soerensen、Soerensen

  DOI：——

  日期：——
• Nakajima, Kenji; Sato, Akio; Takahara, Yoshimasa, Agricultural and Biological Chemistry, 1985, vol. 49, # 7, p. 1993 - 2002
  作者：Nakajima, Kenji、Sato, Akio、Takahara, Yoshimasa、Iida, Takeo

  DOI：——

  日期：——
• Willstaetter; Mayer, Chemische Berichte, 1908, vol. 41, p. 1478
  作者：Willstaetter、Mayer

  DOI：——

  日期：——

表征谱图