Cumyl alcohol

Cumyl alcohol, also called 4-isopropylbenzyl alcohol, is a liquid, hydroxy functional, aromatic organic chemical with formula C10H14O. It has the CAS Registry Number of 536-60-7 and the IUPAC name of (4-propan-2-ylphenyl)methanol.[2][3] It is REACH registered with the EC number of 208-640-4.[4]

Cumyl alcohol
Names
IUPAC name
(4-Propan-2-ylphenyl)methanol
Other names
  • Cuminyl alcohol
  • Cuminol
  • 4-Isopropylbenzyl alcohol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.857
EC Number
  • 208-640-4
UNII
  • InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-6,8,11H,7H2,1-2H3
    Key: OIGWAXDAPKFNCQ-UHFFFAOYSA-N
  • CC(C)C1=CC=C(C=C1)CO
Properties
C10H14O
Molar mass 150.221 g·mol−1
Odor Caraway
Density 0.974-0.982
Melting point 28 °C (82 °F; 301 K)
log P 2.370
1.518-1.525
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P317, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

The most common use is as a food additive to add flavor.[5][6] The material also has insect repellent properties.[7]

Manufacture

Hydrogenation of cuminal can produce cumyl alcohol.[8]

Other

Cumyl alcohol is an undesired side reaction product when LDPE is crosslinked.[9] LDPE is used as a plastic electric insulator for electrical power cables.[10] The cumyl alcohol reduces the insulating properties.[11][12]

Alternative names

Main sources of information.[13][14]

  • p-Cymen-7-ol
  • 4-isopropylbenzyl alcohol
  • Cumic alcohol[15]
  • Cuminol
  • Cuminyl alcohol[16]
  • (4-Isopropylphenyl)methanol
  • Cuminic alcohol

Toxicology

The toxicity of the material has been studied and is reasonably well understood.[17][18][19]

References
  1. "4-Isopropylbenzyl alcohol". pubchem.ncbi.nlm.nih.gov. Retrieved 29 March 2023.
  2. PubChem. "4-Isopropylbenzyl alcohol". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-28.
  3. "4-isopropylbenzyl alcohol". www.wikidata.org. Retrieved 2023-03-28.
  4. "Substance Information - ECHA". echa.europa.eu. Retrieved 2023-03-29.
  5. "P-ISOPROPYLBENZYL ALCOHOL | FEMA". www.femaflavor.org. Retrieved 2023-03-29.
  6. "Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to Flavouring Group Evaluation 20 (FGE.20): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical group 23 | EFSA". www.efsa.europa.eu. 9 January 2006. Retrieved 2023-03-29.
  7. "4-Isopropylbenzyl alcohol | CAS 536-60-7 | SCBT - Santa Cruz Biotechnology". www.scbt.com. Retrieved 2023-03-29.
  8. Cooke, R. G.; Gillespie, D. T.; Macbeth, A. Killen (1938-01-01). "338. Cumyl alcohol". Journal of the Chemical Society (Resumed): 1825–1826. doi:10.1039/JR9380001825. ISSN 0368-1769.
  9. Hirai, N.; Maeno, Y.; Tanaka, T.; Ohki, Y.; Okashita, M.; Maeno, T. (October 2003). "Roles of cumyl alcohol and crosslinked structure in homo-charge trapping in crosslinked polyethylene". 2003 Annual Report Conference on Electrical Insulation and Dielectric Phenomena. pp. 213–216. doi:10.1109/CEIDP.2003.1254831. ISBN 0-7803-7910-1. S2CID 137379755.
  10. Gulmine, J. V.; Akcelrud, L. (2006-10-01). "FTIR characterization of aged XLPE". Polymer Testing. 25 (7): 932–942. doi:10.1016/j.polymertesting.2006.05.014. ISSN 0142-9418.
  11. Chen, Meng; Zhang, Hongliang; Wang, Yalin; Wu, Jiandong; Yin, Yi (February 2020). "Space charge dynamics of acetophenone and cumyl alcohol and their synergistic effect in LDPE". IEEE Transactions on Dielectrics and Electrical Insulation. 27 (1): 67–75. doi:10.1109/TDEI.2019.008320. ISSN 1070-9878. S2CID 211119082.
  12. Hussin, N.; Chen, G. (February 2012). "Analysis of space charge formation in LDPE in the presence of crosslinking byproducts". IEEE Transactions on Dielectrics and Electrical Insulation. 19 (1): 126–133. doi:10.1109/TDEI.2012.6148510. ISSN 1070-9878. S2CID 31136608.
  13. "cuminyl alcohol, 536-60-7". www.thegoodscentscompany.com. Retrieved 2023-03-29.
  14. "p-Cymen-7-ol". webbook.nist.gov. Retrieved 2023-03-29.
  15. "Cumic alcohol | CAS#536-60-7 | insulinotropic agent | MedKoo". medkoo.com. Retrieved 2023-03-29.
  16. "cuminyl alcohol, 536-60-7". www.thegoodscentscompany.com. Retrieved 2023-03-29.
  17. Api, A.M.; Belsito, D.; Biserta, S.; Botelho, D.; Bruze, M.; Burton, G.A.; Buschmann, J.; Cancellieri, M.A.; Dagli, M.L.; Date, M.; Dekant, W.; Deodhar, C.; Fryer, A.D.; Gadhia, S.; Jones, L. (July 2020). "RIFM fragrance ingredient safety assessment, p-isopropylbenzyl alcohol, CAS Registry Number 536-60-7". Food and Chemical Toxicology. 141: 111338. doi:10.1016/j.fct.2020.111338. PMID 32335211. S2CID 216556801.
  18. Patil, Swapnil B.; Takalikar, Shreehari S.; Joglekar, Madhav M.; Haldavnekar, Vivek S.; Arvindekar, Akalpita U. (October 2013). "Insulinotropic and β-cell protective action of cuminaldehyde, cuminol and an inhibitor isolated from Cuminum cyminum in streptozotocin-induced diabetic rats". British Journal of Nutrition. 110 (8): 1434–1443. doi:10.1017/S0007114513000627. ISSN 0007-1145. PMID 23507295.
  19. Ali, Mohd Sajid; Rehman, Md Tabish; Al-Lohedan, Hamad A.; AlAjmi, Mohamed Fahad (2022-12-12). "Exploration of the binding between cuminol and bovine serum albumin through spectroscopic, molecular docking and molecular dynamics methods". Journal of Biomolecular Structure and Dynamics. 40 (22): 12404–12412. doi:10.1080/07391102.2021.1971560. ISSN 0739-1102. PMID 34488560. S2CID 237432888.
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