Dihydromyrcenol

Dihydromyrcenol
Names
IUPAC name
2,6-Dimethyloct-7-en-2-ol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.038.497
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H20O/c1-5-9(2)7-6-8-10(3,4)11/h5,9,11H,1,6-8H2,2-4H3
    Key: XSNQECSCDATQEL-UHFFFAOYSA-N
SMILES
  • CC(CCCC(C)(C)O)C=C
Properties
Chemical formula
 C10H20O
Molar mass 156.269 g·mol−1
Appearance Colorless viscous liquid[1]
Density 0.832 g/cm3 (20 °C)[1]
Boiling point 194–197 °C (381–387 °F; 467–470 K)[1]
Solubility in water
 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).
Infobox references

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]

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. ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b c d 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. ^ a b c "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 article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.