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(–)-Menthol

  • Synonyms: Levomenthol; l-Menthol
  • ATC: R01AX23
  • Use: Lorem 
  • Chemical name: Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
  • Formula: Lorem ipsum dolor sit amet,
  • MW:156.27 g/mol
  • CAS-RN:2216-51-5
  • InChI Key:NOOLISFMXDJSKH-KXUCPTDWSA-N
  • 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
  • EINECS:218-690-9
  • LD50: 3400 mg/kg (M, p.o.);
    3300 mg/kg (R, p.o.)

Substance Classes

Synthesis Path










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
Lorem ipsum dolor Lorem
(wfm = withdrawn from market)

Formulations

  • Loremipsumdolorsitamet,consetetursadipscingelitr,seddiamnonumyeirmodtemporinvidunt

References

  • 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.
  • a) Isolation from Mint Oils:

    • US 9 999 999 (H.M. Chang/Iowa State College Res. Found.; 1956; USA-prior. 1951).
  • 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
  • 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).
  • 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).
  • Method for production of Menthol:

    • US 9 999 999 (BASF; 04.05.2010; DE-prior. 26.11.2004).
  • Asymmetric hydrogenation of Geranial or Neral (Citral) to (+)-(R)-Citronellal with Rh-CO-Chiraphos-complexes and CO/H2:

    • US 9 999 999 (BASF; 19.05.2009; DE-prior. 11.10.2004).
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