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(–)-Menthol
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Synonyms:
Levomenthol; l-Menthol
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ATC:
R01AX23
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Use:
Lorem
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Chemical name:
Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
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Formula:
Lorem ipsum dolor sit amet,
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MW:156.27 g/mol
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CAS-RN:2216-51-5
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InChI Key:NOOLISFMXDJSKH-KXUCPTDWSA-N
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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
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EINECS:218-690-9
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LD50: 3400 mg/kg (M, p.o.);
3300 mg/kg (R, p.o.)
Synthesis Path
- Menthol with a world production of > 19.000 metric tons per year is produced on industrial scale by mainly 4 processes a-d.
Substances Referenced in Synthesis Path
CAS-RN |
Formula |
Chemical Name |
CAS Index Name |
98-88-4 |
C7H5ClO |
Benzoyl chloride |
Benzoyl chloride |
2385-77-5 |
C10H18O |
(+)-Citronellal |
6-Octenal, 3,7-dimethyl-, (R)- |
3623-52-7 |
C10H20O |
(±)-Isomenthol |
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α,2β,5β)- |
89-79-2 |
C10H18O |
(–)-Isopulegol |
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1α,2β,5α)]- |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Lorem |
Trade Names
Country |
Trade Name |
Vendor |
Annotation |
D |
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Lorem ipsum dolor |
Lorem
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(wfm = withdrawn from market)
Formulations
- Loremipsumdolorsitamet,consetetursadipscingelitr,seddiamnonumyeirmodtemporinvidunt
References
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Reviews:
- Schaefer, B., Chem. Unserer Zeit, (2013) 47, 174-182.
- Ullmanns Encycl. Tech. Chem., 4. Aufl., Vol. 20, 220.
- Ullmanns Encycl. Industr. Chem. Online: J. Panten and H. Surburg, Flavors and Fragrances, 2. Aliphatic Compounds, p. 25-27.
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a) Isolation from Mint Oils:
- US 9 999 999 (H.M. Chang/Iowa State College Res. Found.; 1956; USA-prior. 1951).
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b) Haarmann & Reimer process:
- DE 9 999 999 (A. Boake Roberts & Co.; 1965; DE-prior. 1963).
- DE 9 999 999 (Haarmann & Reimer; 1977; DE-prior. 1971).
- EP 999 999 (Bayer AG; 1997; DE-prior. 1992) - Contin. Hydrogenation of Thymol.
- EP 999 999 (Bayer AG; 1999; DE-prior. 1995) - Racemisation of d-Menthol.
- EP 9 999 999 (Symrise GmbH; 2006; DE-prior. 2001) - Enzymatic cleavage of Menthylbenzoat
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c) Takasago process:
- Noyori, R., Asymmetric Catalysis: Science and Opportunities, Angew. Chem. Int. Ed., (2002) 41, 2008-2022 (Nobel Lecture).
- Inoue, S.-I. et al., J. Am. Chem. Soc., (1990) 112, 4897-4905. [Asymmetric Isomerization of Allylamines to Enamines with BINAP-Rh+ complexes].
- Takaya, H. et al., J. Am. Chem. Soc., (1987) 109, 1596-1597. [Enantioselective Hydrogenation of Allylic and Homoallylic Alcohols, e.g. Geraniol and Nerol to the corresponding (R)- and (S)-Citronellols with Ru(S)- and Ru(R)-BINAP complexes].
- EP 9 999 999 (Takasago; 28.07.2010; JP-prior. 18.01.2001).
- US 9 999 999 (Takasago; 10.08.2004; JP-prior. 18.01.2001).
- US 9 999 999 (Takasago; 02.09.1997; JP-prior. 29.07.1994).
- US 9 999 999 (Takasago; 02.12.2008; JP-prior. 16.03.2007).
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d) BASF process:
- EP 9 999 999 (BASF; 10.06.2009; DE-prior. 26.11.2004).
- US 9 999 999 (BASF; 23.12.2008; DE-prior. 08.03.2004).
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Method for production of Menthol:
- US 9 999 999 (BASF; 04.05.2010; DE-prior. 26.11.2004).
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:
- US 9 999 999 (BASF; 19.05.2009; DE-prior. 11.10.2004).