(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

• ChemBase编号: 704
• 分子式: C10H20O
• 平均质量: 156.2652
• 单一同位素质量: 156.15141526
• SMILES: O[C@H]1[C@@H](CC[C@H](C1)C)C(C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
• InChI: InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
• InChIKey: NOOLISFMXDJSKH-KXUCPTDWSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
• IUPAC传统名: menthol
• 别名: (-)-薄荷醇; (1R,2S,5R)-2-异丙基-5-甲基环己醇; 5-甲基-2-异丙基环己醇; L-薄荷醇; L-薄荷醇晶体; 5-甲基-2-(1-甲基乙基)环己醇; (-)-薄荷醇; L-薄荷醇; (1R,2S,5R)-2-isopropyl-5-methylcyclohexanol; L-Menthol; (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanol; [1R-(1α,2β,5α)]-5-Methyl-2-(1-methylethyl)cyclohexanol; (-)-(1R,3R,4S)-Menthol; (-)-Menthyl Alcohol; (-)-trans-p-Methan-cis-3-ol; (1R)-(-)-Menthol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexan-1-ol; (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanol; 1R-Menthol; L-Mentholum; Minclea; NSC 62788; (1R,2S,5R)-(-)-Menthol; (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol; (-)-menthol; L-menthol; L-(-)-menthol; (r)-(-)-menthol; Levomenthol; Menthol; 5-Methyl-2-(1-methylethyl)-cyclohexanol; L-MENTHOL; (1R,2S,5R)-(-)-Menthol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol; 5-Methyl-2-(1-methylethyl)cyclohexanol; L-Menthol crystals; 3-p-Menthanol; Hexahydrothymol; Menthomenthol; peppermint camphor; (-)-Menthol; (1R,2S,5R)-(-)-Menthol

登记号

• CAS号: 89-78-1; 2216-51-5
• EC号: 218-690-9
• MDL号: MFCD00062979
• Beilstein号: 1902293
• PubChem SID: 24896767; 24882791; 24849703; 24901228; 46506513; 160964167; 24881231; 24901227; 24901229
• PubChem CID: 16666
• CHEBI ID: 15409
• CHEMBL: 470670
• Chemspider ID: 15803
• DrugBank ID: DB00825
• FEMA编号: 2665
• 美国药典/FDA物质标识码: YS08XHA860
• 维基百科标题: Menthol
• 欧洲委员会编号: 65c

理论计算性质

JChem

• Acid pKa: 19.549648
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 2.664273
• LogD (pH = 7.4): 2.6642733
• Log P: 2.6642733
• 摩尔折射率: 47.4453 cm^3
• 极化性: 19.046404 Å^3
• 极化表面积: 20.23 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.68
• LOG S: -2.45
• 溶解度: 5.58e-01 g/l

分子性质

理化性质

• 溶解度: 0.49 mg/mL at 25 oC [CHEM INSPECT TEST INST (1992)]; Slightly soluble, (−)-isomer
• 外观: White or colorless; crystalline solid
• 熔点: ~43 °C; 36–38 °C (311 K), racemic; 42–45 °C (318 K), (−)-form (α); 35-33-31 °C, (−)-isomer; 41-44 °C; 41-45 °C(lit.); 43°C
• 沸点: 212 °C(lit.); 212°C; 212 °C (485 K)
• 闪点: 101 °C; 213.8 °F; 93 °C
• 密度: 0.89 g/mL at 25 °C(lit.); 0.890 g·cm^−3, solid; (racemic or (−)-isomer)
• 蒸汽压: 0.8 mmHg ( 20 °C)
• 比旋光度: [α]20/D -48 to -51°, c = 10% in ethanol; [α]20/D -49°, c = 10 in 95% ethanol; [α]20/D -50±1°, c = 10% in ethanol; [α]20/D -50°, c = 10 in ethanol; [α]20/D -50°, c = 10% in ethanol; [α]22/D -49°, c = 10 in 95% ethanol
• 疏水性(logP): 3.2; 3.233
• 感官: camphoraceous; tobacco; minty; minty; camphoraceous; minty; woody; camphoraceous; tobacco

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: OT0350000, racemic; OT0700000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 37/38-41; R:36/37/38; R37/38, R41
• 安全公开号: 26-39; S:20-25-26-37/39; S26, S36
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• 主要危害: Irritant, flammable
• GHS危险声明: H315-H318-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: FCC

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥99%; ≥99.0% (sum of enantiomers, GC); 95%; 95+%; 99%
• 级别: analytical standard, for terpene analysis; Halal; Kosher; natural; NI; primary reference standard; puriss.; ReagentPlus®
• 光学纯度: ee: 99% (GLC); enantiomeric ratio: ≥99:1 (GC)
• 适用性: in accordance for appearance of solution
• 简要说明: L-isomer
• 杂质: ≤0.05% non-volatile matter; acidity or alcalinity, complies; chromatographic purity (GC), complies; related subst., complies; residual solvents, complies
• 有效期: (limited shelf life, expiry date on the label)
• 品质说明: meets analytical specification of Ph. Eur., BP, USP
• Empirical Formula (Hill Notation): C10H20O
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 05214994

MP Biomedicals Rare Chemical collection

DrugBank - DB00825

• Drug Groups: approved
• Description: Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.
• Indication: Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.
• Pharmacology: Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol's ability to chemically trigger cold-sensitive receptors in the skin is responsible for the well known cooling sensation that it provokes when inhalated, eaten, or applied to the skin. It should be noted that menthol does not cause an actual drop in temperature.
• Toxicity: Menthol, DL: ORAL (LD50): Acute: 2900 mg/kg [Rat], 3100 mg/kg [Mouse]. DERMAL (LD50): Acute: 5001 mg/kg [Rabbit].
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - 588733

包装
1 g in glass bottle

Sigma Aldrich - W266558

Biochem/physiol Actions
25ppm 时的味道
General description
天然存在：薄荷。

Sigma Aldrich - W266590

Biochem/physiol Actions
25ppm 时的味道
General description
天然存在：薄荷。
包装
1 kg in poly bottle
1 sample in glass bottle
4, 9, 25 kg in fiber drum

Sigma Aldrich - W266523

Biochem/physiol Actions
25ppm 时的味道
Other Notes
天然存在：薄荷。
包装
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
4 kg in fiber drum

Sigma Aldrich - 63660

Other Notes
用作酸的重要拆分剂，最新的用途包括1：结晶诱导不对称转换丙二酸盐2；手性辅助剂3,4

Sigma Aldrich - M2780

包装
25, 100, 500 g in poly bottle
Application
制备用于手性插烯 Darzens 和 Reformatsky 反应的试剂。1用于酸的拆分以及立体控制合成的重要手性助剂。2
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M218875

(1R,2S,5R)-(-)-Menthol (L-Menthol) is the natural form of Menthol. L-Menthol is used as: refreshing agent, food flavor, cool and antipruritic drug, carminative drug. Menthol crystals is used for personal care and cosmetics.

参考文献

• Ikaheimo, I., et al.: J. Antimicrob. Chemother., 46, 287 (2000)
• Gillet, Y., et al.: Lancet, 359, 753 (2000)
• Turos, E., et al.: Bioorg. Med. Chem. Lett., 2002, 12, 2229 (2000)
• Costa, S., et al.: Toxicology, 252, 40 (2000)