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 is one approach.[8] It is also produced as an intermediate or by-product in the manufacture of cumene hydroperoxide and propylene oxide. The oxidation of propylene using cumene hydroperoxide as the oxygen donor produces propylene oxide and cumyl alcohol as a by product.[9] Sumitomo Chemical have a three-stage process in which the end goal is to produce Cumene hydroperoxide. The glycidation (epoxidation) process involving propylene oxide at the next stage along with the hydroperoxide produces cumyl alcohol as an intermediate (or finished product).[10][11]

Other

Cumyl alcohol is an undesired side reaction product when LDPE is crosslinked.[12] LDPE is used as a plastic electric insulator for electrical power cables.[13] The cumyl alcohol reduces the insulating properties.[14][15]

Alternative names

Main sources of information.[16][17]

  • p-Cymen-7-ol
  • 4-isopropylbenzyl alcohol
  • Cumic alcohol[18]
  • Cuminol
  • Cuminyl alcohol[19]
  • (4-Isopropylphenyl)methanol
  • Cuminic alcohol

Toxicology

The toxicity of the material has been studied and is reasonably well understood.[20][21][22]

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. 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. Tang, Kang; Hou, Weilong; Wang, Xiaoshu; Xu, Wen; Lu, Xinqing; Ma, Rui; Fu, Yanghe; Zhu, Weidong (2021-12-01). "Enhanced catalytic performance of trimethylsilylated Ti-MWW zeolites for the liquid-phase epoxidation of propylene with H2O2". Microporous and Mesoporous Materials. 328: 111492. doi:10.1016/j.micromeso.2021.111492. ISSN 1387-1811. S2CID 242938571.
  10. Kawabata, Tomonori; Yamamoto, Jun; Koike, Hirofumi; Yoshida, Shuhei. "Trends and Views in the Development of Technologies for Propylene Oxide production (translated from Japanese)" (PDF).
  11. "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
  12. 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: 213–216. doi:10.1109/CEIDP.2003.1254831. ISBN 0-7803-7910-1. S2CID 137379755.
  13. 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.
  14. 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.
  15. 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.
  16. "cuminyl alcohol, 536-60-7". www.thegoodscentscompany.com. Retrieved 2023-03-29.
  17. "p-Cymen-7-ol". webbook.nist.gov. Retrieved 2023-03-29.
  18. "Cumic alcohol | CAS#536-60-7 | insulinotropic agent | MedKoo". medkoo.com. Retrieved 2023-03-29.
  19. "cuminyl alcohol, 536-60-7". www.thegoodscentscompany.com. Retrieved 2023-03-29.
  20. 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.
  21. 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.
  22. 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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