Dihydromyrcenol

Last updated
Dihydromyrcenol
Dihydromyrcenol.svg
Names
IUPAC name
2,6-Dimethyloct-7-en-2-ol
Identifiers
3D model (JSmol)
DrugBank
PubChem CID
UNII
  • CC(CCCC(C)(C)O)C=C
Properties
C10H20O
Molar mass 156.269 g·mol−1
AppearanceColorless viscous liquid [1]
Density 0.832 g/cm3 (20 °C) [1]
Boiling point 194–197 °C (381–387 °F; 467–470 K) [1]
0.939 g/L (20 °C) [1]
Hazards
Flash point 76 °C (169 °F; 349 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dihydromyrcenol is a synthetic organic compound used primarily as a fragrance ingredient. Despite its similarity to some natural compounds of the monoterpene class, such as myrcenol, it has not been reported to be found in nature. [2]

Contents

Chemical properties

Dihydromyrcenol has the chemical formula C10H20O. [3] It is a colorless viscous liquid with a boiling point of 194–197 °C (381–387 °F). [1]

Odor and uses

Dihydromyrcenol is extensively used in the fragrance industry for its fresh lime and citrus-like odor. [2] Descriptions of its scent include citrus type, [4] lime-like citrusy-floral sweet with considerable tenacity, [2] fresh citrus-like with a lavender note, [5] fresh cool metallic lime citrus floral bergamot, [6] and lavender fragrance reminiscent of lemon. [7] Worldwide use exceeded 1000 metric tons per year as of 2004. [5]

Synthesis

Dihydromyrcenol can be obtained from citronellene, a pyrolysis product of cis-pinane, via hydroxylation. [8] [9] [5]

Safety

A toxicologic and dermatologic review has been published on its use as a fragrance ingredient and it is considered safe under regulated use. [2]

References

  1. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 4 McGinty, D.; Letizia, C.S.; Api, A.M. (2010). "Fragrance material review on dihydromyrcenol". Food and Chemical Toxicology. 48: S70–S75. doi:10.1016/j.fct.2009.11.014. PMID   20141881.
  3. ↑ CID 29096 from PubChem
  4. ↑ "Dihydromyrcenol: 2,6-dimethyloct-7-en-2-ol".
  5. 1 2 3 "Dihydromyrcenol".
  6. ↑ "Dihydro Myrcenol".
  7. ↑ "Dihydromyrcenol".
  8. ↑ Naves, Y -R (1968). "Progress in the Synthesis of Perfumes Based on Pinenes". Russian Chemical Reviews. 37 (10): 779–788. Bibcode:1968RuCRv..37..779N. doi:10.1070/RC1968v037n10ABEH001703.
  9. ↑ Prajapati, Rupali S.; Bhanage, Bhalchandra M. (2025). "Hydroformylation, hydroaminomethylation and related tandem reactions of bio-derived renewable olefins: A step closer to sustainability". RSC Sustainability. 3: 158–207. doi:10.1039/d4su00662c.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.