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CS-W001157 4
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(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanecarboxylic acid

  • CAS No. 16052-40-7

  • Cat. No. CS-B1297
  • Purity≥97%
  • MDL No.MFCD00798812

*For research and further manufacturing use only, not for direct human use.

(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanecarboxylic acid|CS-B1297

Structure of 16052-40-7

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General Information

  • CAS No. 16052-40-7
  • Cat. No. CS-B1297
  • Purity ≥97%
  • MDL No. MFCD00798812
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₀O₂
  • Molecular Weight None
  • Synonym(s) (1R,3R,4S)-p-Menthane-3-carboxylic acid; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarboxylic acid
  • SMILES O=C([C@H]1[C@H](C(C)C)CC[C@@H](C)C1)O

Description

(-)-Menthylformic acid is a chiral ester featuring a formate group attached to a menthol-derived scaffold. This configuration imparts high stereochemical integrity and stability under standard bench conditions. The molecule integrates readily into asymmetric synthesis workflows, where its steric profile and solubility in organic media enable efficient derivatization. Its robustness facilitates handling in process development without decomposition.

Application

(-)-Menthylformic acid serves as a chiral building block for asymmetric synthesis, leveraging the rigid, naturally occurring menthyl scaffold to direct stereochemistry in subsequent transformations. Its formate ester functionality enables controlled reactivity in nucleophilic substitutions and reductions, while the stable, crystalline solid form facilitates handling and purification. Widely used in fragrance and pharmaceutical intermediates, it functions as a versatile, bench-stable precursor for stereoselective derivatization.

Synthesis

  • Route1
    • null|null
      80434-59-9
    • ~97%
    • In-stock
      (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanecarboxylic acid|CS-B1297
      16052-40-7

    References

    • Spino, Claude; Gobdout, Cedrickx Journal of the American Chemical Society, 2003 , vol. 125, # 40 p. 12106 - 12107
  • Route2
    • null|null
      124-38-9
    • (1S,2R,4R)-2-chloro-1-isopropyl-4-methylcyclohexane|CS-0328614
      16052-42-9
    • ~39%
    • In-stock
      (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanecarboxylic acid|CS-B1297
      16052-40-7

    References

    • GENENTECH, INC. Patent: WO2005/2582 A2, 2005 ; Location in patent: Page 45-46 ;
  • Route3
    • null|null
      663218-94-8
    • ~%
    • In-stock
      (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanecarboxylic acid|CS-B1297
      16052-40-7

    References

    • US2012/283469 A1, ; Page/Page column 4 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.7794
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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