松油醇 | 98-55-5

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 醇的卤化、磺化、硝化或亚硝化衍生物
• 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: 松油醇
• 中文别名: α-萜品醇；1-萜烯-8-醇；2-(4-甲基-3-环己烯基)-2-丙醇；alpha-松脂醇；α-松油醇；alpha-松油醇；Alpha-萜品醇
• 英文名称: terpineol
• 英文别名: α-terpineol；p-menth-1-en-8-ol；(+/-)-alpha-Terpineol；α-terpinol；2-(4-methylcyclohex-3-en-1-yl)propan-2-ol；α,α,4-trimethyl-3-cyclohexene-1-methanol；l-α-terpineol；α-terpineole；4-terpineol；a-terpineol；2-(4-methyl-3-cyclohexen-1-yl)-2-propanol；2-(4-methylcyclohex-3-enyl)propan-2-ol；(±)-α-terpineol；α-terpeneol；α-terpeniol；(±)-2-(4-methylcyclohex-3-en-1-yl)propan-2-ol；4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol；α-terpinenol；alfa terpineol；1-terpineol；1,1-dimethyl-1-(4-methylcyclohex-3-enyl)methanol；terpineol-alpha；Alpha-Terpineol
• CAS: 98-55-5；8000-41-7
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: WUOACPNHFRMFPN-UHFFFAOYSA-N

物化性质

• 熔点：
  18°C
• 沸点：
  213-218 °C (lit.)
• 密度：
  0.934 g/mL at 20 °C (lit.)
• 闪点：
  95°C
• 溶解度：
  乙醇：可溶1.25ml/10ml，澄清至微浑浊，无色至浅黄色（50%乙醇）
• 介电常数：
  2.8（20℃）
• LogP：
  3.330 (est)
• 物理描述：
  Liquid
• 颜色/状态：
  Colorless solid
• 气味：
  Floral, lilac
• 味道：
  Lime (distilled)
• 蒸汽压力：
  0.0423 mm Hg at 24 °C
• 亨利常数：
  2.23e-06 atm-m3/mole
• 稳定性/保质期：

  Chemical stability: Stable under recommended storage conditions.

• 旋光度：
  Specific optical rotation: 106.4 deg at 20 °C/D
• 分解：
  When heated to decomp it emits acrid smoke and irritating fumes.
• 气味阈值：
  Aroma threshold values: Detection: 280-350 ppb
• 折光率：
  Index of refraction: 1.4831 at 20 C/D
• 保留指数：
  1209;1198

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

对雄性白化大鼠口服给予alpha-terpineol的代谢命运进行了研究，并对其对肝脏微粒体细胞色素P-450系统的影响进行了探讨。为了进行代谢研究，每天一次给予alpha-terpineol，连续20天，剂量为600mg/kg体重；细胞色素P-450研究涉及最多9天的给药。...分离出的中性馏分显示存在一个主要成分（alpha-terpineol）和两个次要化合物。其中一个次要化合物被鉴定为p-薄荷烷-1,2,8-三醇。进一步的研究揭示了橄榄酸和二氢橄榄酸的甲基酯的存在。碳-1位置的烯丙基甲基酯的氧化似乎是主要的代谢途径。考虑到烯丙基甲基团在C-7位置的氧化可能发生在1,2-双键还原之前。给予alpha-terpineol后，肝脏微粒体细胞色素P-450的水平在给药1、2、3、6和9天后分别增加了72%、104%、90%、54%和52%。在重复给药的前3天内，肝脏微粒体NADPH-细胞色素c-还原酶的水平有所中度增加。对细胞色素b5和NADH-细胞色素c-还原酶没有显著影响。作者得出结论，alpha-terpineol的烯丙基甲基氧化是其在大鼠体内代谢转化的主要途径。特别注意到，在橄榄酸形成二氢橄榄酸的过程中，内环双键的还原。

The metabolic fate of alpha-terpineol administered orally to male albino-rats was investigated, and its effects on the liver microsomal cytochrome-P-450 system were studied. For metabolic studies, alpha-terpineol was given once daily for 20 days at a dose of 600mg/kg bw; cytochrome-P-450 studies involved dosing for up to 9 days. ...The neutral fraction isolated showed the presence of one major (alpha-terpineol) and two minor compounds. One of the minor compounds was identified as p-menthane-1,2,8-triol. Further study revealed the presence of the methyl esters of oleuropeic-acid and dihydrooleuropeic-acid. Allylic oxidation of C-1 methyl esters appeared to be the major metabolic pathway. It was considered likely that the allylic methyl group at C-7 was oxidized prior to the reduction of the 1,2-double bond. Administration of alpha-terpineol increased the levels of liver microsomal cytochrome-P-450 by 72, 104, 90, 54, and 52% after 1, 2, 3, 6, and 9 days of dosing, respectively. A moderate incr was noted in the levels of liver microsomal NADPH-cytochrome-c-reductase during the first 3 days of repeated dosing. No significant effect was noted on cytochrome-b5 and NADH-cytochrome-c-reductase. The authors conclude that the allylic methyl oxidation of alpha-terpineol is the major route for its metabolic transformation in the rat. The reduction of the endocyclic double bond was specifically noted in the formation of dihydrooleuropeic-acid from oleuropeic-acid.

来源:Hazardous Substances Data Bank (HSDB)

代谢

松节油通过普通夜蛾（Spodoptera litura）幼虫的生物转化被研究。将松节油混合在人造饲料中，然后将饲料喂给S. litura的幼虫（第四至第五龄幼虫）。从幼虫的粪便中分离出代谢物并进行光谱分析。主要代谢物是7-羟基-松节油（p-薄荷-1-烯-7,8-二醇）和橄榄酸（8-羟基-p-薄荷-1-烯-7-酸）。幼虫粪便中的肠道细菌没有参与松节油的代谢。松节油被S. litura幼虫优先在C-7位置（烯丙基甲基基团）氧化。

Biotransformation of alpha-terpineol by the common cutworm (Spodoptera litura) larvae was investigated. alpha-Terpineol was mixed in an artificial diet, and the diet was fed to the larvae (fourth-fifth instar) of S. litura. Metabolites were isolated from the frass and analyzed spectroscopically. Main metabolites were 7-hydroxy-alpha-terpineol (p-menth-1-ene-7,8-diol) and oleuropeic acid (8-hydroxy-p-menth-1-en-7-oic acid). Intestinal bacteria from the frass of larvae did not participate in the metabolism of alpha-terpineol. alpha-Terpineol was preferentially oxidized at the C-7 position (allylic methyl group) by S. litura larvae.

来源:Hazardous Substances Data Bank (HSDB)

代谢

以下是细长金黄杆菌对 alpha-terpineol 的新陈代谢细节。这种微生物对 alpha-terpineol 的降解产生了一系列酸性代谢物和中性代谢物。在酸性代谢物中，已经鉴定出了 beta-异丙基戊二酸、1-羟基-4-异丙烯基环己烷-1-羧酸、8-羟基枯酸、橄榄酸、枯酸和 p-异丙烯基苯甲酸。鉴定出的中性代谢物包括柠檬烯、p-对伞花烃-8-醇、2-羟基桉叶油醇和尿 terpenol。...看起来细长金黄杆菌至少通过三种不同的途径降解 alpha-terpineol。其中一条途径似乎是通过橄榄酸进行的，第二条途径可能是由 alpha-terpineol 的芳构化启动的。第三条途径可能涉及从 alpha-terpineol 形成柠檬烯及其进一步的代谢。

Details of the metabolism of alpha-terpineol by Pseudomonas incognita are presented. Degradation of alpha-terpineol by this organism resulted in the formation of a number of acidic and neutral metabolites. Among the acidic metabolites, beta-isopropyl pimelic acid, 1-hydroxy-4-isopropenyl-cyclohexane-1-carboxylic acid, 8-hydroxycumic acid, oleuropeic acid, cumic acid, and p-isopropenyl benzoic acid have been identified. Neutral metabolites identified were limonene, p-cymene-8-ol, 2-hydroxycineole, and uroterpenol. ... /I/t appears that P. incognita degrades alpha-terpineol by at least three different routes. While one of the pathways seems to operate via oleuropeic acid, a second may be initiated through the aromatization of alpha-terpineol. The third pathway may involve the formation of limonene from alpha-terpineol and its further metabolism.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在一条次要途径中，alpha-terpineol 的内环烯烃被环氧化，然后水解产生一个三醇代谢物 1,2,8-三羟基-对-孟烷，这也曾报道过在人类意外口服含有 alpha-terpineol 的松油消毒剂后的情况。

In a minor pathway, the endocyclic alkene of alpha-terpineol is epoxidized and then hydrolysed to yield a triol metabolite 1,2,8-trihydroxy- para-menthane, which was also reported in humans after inadvertent oral ingestion of a pine-oil disinfectant containing alpha-terpineol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

主要通过与葡萄糖醛酸结合进行代谢，并以尿液形式排出体外。烯丙基甲基团的氧化随后通过氢化生成相应的饱和酸可能发生。

Metabolized primarily by conjugation with glucuronic acid and excreted in urine. Oxidation of the allylic methyl group followed by hydrogenation to yield the corresponding saturated acid may occur.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：alpha-松油醇是一种无色固体。它用于香水制造；将脂肪变性以用于肥皂制造；烃类溶剂；用于树脂、纤维素酯和醚的溶剂；消毒剂；抗氧化剂；药物；香料成分。在美国，它目前没有注册为农药使用，但批准的农药用途可能会定期更改，因此必须咨询联邦、州和地方当局以获取当前批准的用途。人类暴露和毒性：在人类受试者中，alpha-松油醇具有较低的刺激性但强烈的气味。据报道，两名皮炎患者对alpha-松油醇敏感，尽管尝试使用稀释的alpha-松油醇溶液在志愿者中诱导皮肤敏感化并未成功。文献中描述的两起死亡案例均是由于意外摄入含有松油的产品，归因于异丙醇和1-alpha-松油醇的联合毒性。评估了互叶白千层精油（茶树油）对体外激活的人外周血白细胞产生氧衍生活性物种的调节特性，发现alpha-松油醇显著抑制了fMLP-、LPS-和PMA刺激的超氧阴离子产生；这表明这些成分在炎症期间对细胞类型的选择性调节潜力。动物研究：在兔子中，纯alpha-松油醇是一种中等程度的皮肤刺激物。在急性口服暴露后，啮齿类动物通常报告低毒性。研究了松油（一种商业上可用的消毒剂）在马中静脉给药后的急性毒性。alpha-松油醇被识别为松油的主要成分。在静脉注射0.1 mL/kg后，从马的组织中回收了alpha-松油醇，由于大量肺水肿，几分钟内死亡。在大鼠重复口服给药后，看到了肝脏影响的间接证据。在小鼠（通过注射治疗）的有限研究中没有看到肺致癌性的迹象。Terpineol在没有和有激活的情况下，都导致了Salmonella TA102测试菌株的his+回复突变体数量略有但与剂量相关的增加。研究了terpineol对大鼠坐骨神经复合动作电位（CAP）的影响。Terpineol诱导了CAP的剂量依赖性阻塞。

IDENTIFICATION AND USE: alpha-Terpineol is a colorless solid. It used in perfumes manufacturing; denaturing fats for soap manufacture; hydrocarbon solvent; solvent for resins, cellulose esters, and ethers; disinfectants; antioxidants; medicines; constituent of flavorings. It is not registered for current pesticide use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: In human subjects, alpha-terpineol had a low irritative potency but a strong odor. Two dermatitis patients were reported to be sensitized to alpha-terpineol, although attempts to induce skin sensitization in volunteers using a dilute solution of alpha-terpineol were unsuccessful. Two fatalities described in the literature were both due to accidental ingestion of a pine oil-containing products and were attributed to combined toxicity of isopropanol and 1-alpha-terpineol. The regulatory properties of the essential oil of Melaleuca alternifolia (tea tree oil) on the production of oxygen derived reactive species by human peripheral blood leukocytes activated in vitro was evaluated and found that alpha-terpineol significantly suppressed fMLP-, LPS- and PMA-stimulated superoxide production; suggesting the potential for selective regulation of cell types by these components during inflammation. ANIMAL STUDIES: In rabbits neat alpha-terpineol was a moderate skin irritant. Following acute oral exposure, a low toxicity was generally reported in rodents. Acute toxicity of pine oil (a commercially available disinfectant) after intravenous administration in horses was studied. alpha-Terpineol was identified as a major constituent of pine oil. alpha-Terpineol was recovered from equine tissues after iv injection of 0.1 mL/kg, death due to massive pulmonary edema occurred within minutes. Indirect evidence of liver effects was seen in rats given repeated oral doses. No indication of lung carcinogenicity was seen in a limited study in mice (treated by injection). Terpineol caused a slight but dose-related increase in the number of his+ revertants with Salmonella TA102 tester strain both without and with activation. The effects of terpineol on the compound action potential (CAP) of rat sciatic nerve were studied. Terpineol induced a dose-dependent blockade of the CAP.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 急性溶剂综合症 职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。 皮肤致敏剂 - 一种可以诱导皮肤过敏反应的剂。

Neurotoxin - Acute solvent syndrome Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

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

毒理性

• 解毒与急救

胃肠净化。由于有吸入性肺炎的高风险，诱导呕吐在这些中毒情况下通常被认为是禁忌的。然而，由于胃黏膜的直接刺激，可能会发生自发呕吐。如果病人在摄入后一小时内就诊并且摄入了大量物质，可以考虑通过插管和灌洗来排空胃内容物……。然而，一些研究表明，与使用吐剂诱导呕吐相比，灌洗的并发症发生率更高。没有证据表明活性炭在这些中毒情况下有帮助。……/松油/

Gastrointestinal decontamination. Since there is a high risk of aspiration pneumonia, induced emesis is usually considered contraindicated in these poisonings. However, spontaneous emesis may occur due to direct irritation of the gastric mucosa. If the patient is seen within an hour of ingestion and a large amount has been ingested, gastric emptying by intubation and lavage may be considered ... . However, some studies have suggested greater rates of complications with lavage than with ipecac-induced emesis. There is no evidence that activated charcoal is helpful in these poisonings. ... /Pine oil/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

眼睛去污。如果眼睛接触到有害物质，应进行大量冲洗。

Eye decontamination. If eye exposure has occurred, copious irrigation of the eyes is appropriate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

肺部症状。在任何显著摄入后，应至少观察患者六小时，以观察任何症状的出现，尤其是肺部症状。如果观察到任何肺部症状，患者应进行胸部X光检查和氧合测量，并且应住院治疗。对于严重的肺部症状，通常应转移到重症监护病房。对于严重的吸入，应按照公认的医学实践处理，就像处理任何严重的吸入性肺炎一样。其他严重的系统性影响也应按照公认的医学实践进行治疗。

Pulmonary symptoms. The patient should be observed for at least six hours with any significant ingestion in order to observe the onset of any symptoms, particularly pulmonary symptoms. If any pulmonary symptoms are observed, the patient should have a chest film and measurement of oxygenation, and hospitalization is appropriate. With severe pulmonary symptoms, transfer to an intensive care unit is usually appropriate. With severe aspiration, management should be handled as in any severe aspiration pneumonia, in accordance with accepted medical practice. Other severe systemic effects should be treated in accordance with accepted medical practice.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 在静脉注射0.1毫升/公斤后，由于大量肺水肿，几分钟内死亡。在这些动物中观察到alpha-松油醇的血和组织水平在150至300 ppm之间。在较小剂量的松油（0.033毫升/公斤）后，马匹存活直到48小时后被安乐死。在这些动物中，有一只在2小时后alpha-松油醇的血药浓度变得无法检测，并且在尸检时未检测到组织中的水平....

... After iv injection of 0.1 mL/kg, death due to massive pulmonary edema occurred within minutes. In this animal blood and tissue levels of alpha-terpineol of between 150 and 300 ppm were observed. After smaller doses of pine oil (0.033 mL/kg), horses survived until euthanized up to 48 hr later. Blood levels of alpha-terpineol became undetectable in one of these animals after 2 hr, and no tissue levels were detected at postmortem....

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S37
• 危险类别码：
  R38
• WGK Germany：
  1
• 海关编码：
  29061400
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  WZ6700000
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319
• 危险性防范说明：
  P305 + P351 + P338

制备方法与用途

概述

电子级松油醇专为印刷电路板清洗应用而设计，用于清除印刷电路板表面的助焊剂。

香料

松油醇具有类似松木和丁香的香气。它是一种粘性液体，但在一定条件下易结晶。沸点在218～219℃之间，在85℃/400Pa时沸腾，在35℃时（α-松油醇）会结晶。主要用于调配紫丁香、铃兰、金合欢和橙花等香型的香皂、化妆品香精，纯α-松油醇还可以用于制造柠檬、橙子和桃子等食用香精。以松油醇为原料制备的各种酯类化合物也是优质的香料。

理化性质

松油醇有α、β、γ三种异构体，在市场上多呈液态，主要用途是作为香料或药用。它的急性毒性数据如下：口服LD50值为4.3g/kg（大鼠），皮下注射LD50大于3g/kg（兔子）。

香料规格与药用规格

香料级松油醇具有良好的香气适应性和稳定性，广泛应用于各种用途的香精配方中。在调合香皂和化妆品香料以及制造类似紫丁香香气的高级香精时也有广泛应用，并可用于制药、电机和油墨等工业。

合成方法与化学性质

合成方法包括使用松节油与硫酸反应生成水合萜二醇晶体，再进行脱水步骤。其无色液体或低熔点透明结晶体，具有丁香味，1份松油醇可溶于2份（体积）70%的乙醇溶液中，微溶于水和甘油。

用途

松油醇广泛用于医药、农药、塑料、肥皂和油墨工业中。同时它也是玻璃器皿上色彩的溶剂，并大量作为矿物浮选起泡剂，如铜矿、铅锌矿等有色金属矿和粉煤的浮选，也用作印染助剂、颜料湿润剂、油漆抗结皮剂、绵羊皮脱脂剂及环氧树脂流平剂。

合成松油的主要成分

合成松油含有较高的萜品油烯，不含有茴香脑和甲基佳味酚，并存在痕量樟脑。水蒸气蒸馏所得松油含龙脑和茴香脑较多。

毒性

根据RIFM提供的资料，松油醇的急性毒性数据：口服LD50为4.3g/kg（大鼠），皮试LD50大于3g/kg（兔子）。

用途总结

松油醇分为香料规格和药用规格两种。香料级松油醇具有较好的香气适应性和稳定性，广泛用于各种用途的香精配方中，并作为增加新鲜气息剂；在百合、紫丁香、铃兰、金合欢等香精中是重要香料，在玉兰、栀子、水仙和松针型香精中也是重要成分。含醇量40%～80%的馏份则称合成松油，主要用于有色金属的浮选起泡剂。