Terpineol   中文名称: 松油醇

Absorption, Distribution and Excretion
... 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....

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Metabolism / Metabolites
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.
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.
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.
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.
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.

Toxicity Summary
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.

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Toxicity Data
LC50 (rat) > 4,760 mg/m3/4hr

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Non-Human Toxicity Values
LD50 Rat oral 5170 mg/kg
LD50 Mouse oral 12,080 ug/kg
LD50 Mouse im 2000 mg/kg
LD50 Mouse (CD-1, male) oral 2830 mg/kg (95% C. I., 2290-3497 mg/kg)

[1]. Sensitive determination of monoterpene alcohols in urine by HPLC–FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates[J]. Journal of Chromatography B, 2008, 875(2): 444-450.

Alpha-terpineol is a terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2. It has a role as a plant metabolite.
alpha-TERPINEOL has been reported in Camellia sinensis, Callistemon citrinus, and other organisms with data available.
2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol is a metabolite found in or produced by Saccharomyces cerevisiae.
See also: Coriander Oil (part of); Peumus boldus leaf (part of); Cannabis sativa subsp. indica top (part of).

154.135

8000-41-7

68540-43-2 (hydrochloride salt)

17100

Colorless solid
Pure alpha-isomer is white, crystalline powder

0.9±0.1 g/cm3

217.5±0.0 °C at 760 mmHg

18°C

89.4±0.0 °C

0.0±0.9 mmHg at 25°C

1.483

2.79

20.23

1

1

1

11

168

0

WUOACPNHFRMFPN-UHFFFAOYSA-N

InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

2-(4-methylcyclohex-3-en-1-yl)propan-2-ol

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。