Structure Database (LMSD)

Common Name
terpinolene
Systematic Name
1-methyl-4-(propan-2-ylidene)cyclohexene p-mentha-1,4(8)-diene
Synonyms
  • 1,4(8)-p-menthadiene
  • 1-methyl-4-(1-methylethylidene)-1-cyclohexene
  • 1-methyl-4-(1-methylethylidene)cyclohexene
  • 4-isopropylidene-1-methylcyclohexene
  • Terpinolen
  • Terpinolene
  • alpha-terpinolene
  • isoterpinene
  • terpinolene
LM ID
LMPR0102090062
Formula
C10H16
Exact Mass
Calculate m/z
136.1252
Status
Curated
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Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C10 isoprenoids (monoterpenes) [PR0102]
Menthane monoterpenoids [PR010209]

Biological Context

Terpinolene is a monoterpene found in the essential oils of various plants, including C. sativa, and has diverse biological activities including antiproliferative and antioxidant properties.1,2,3,4,5 It inhibits expression of AKT1 in Jurkat and K562 cells by 95% when used at a concentration of 0.05% and inhibits the growth of K562 cells when used at a concentration of 0.01%.3 Terpinolene also inhibits the growth of HT-29, Hep-2, NCI-292, and HL-60 cells (IC50s = 16.7, 13.7, 17.4, and 28.8 μg/ml, respectively).4 In cultured human blood cells, terpinolene (10-75 mg/L) increases total antioxidant capacity (TAC), but decreases cell viability when used at a concentration of ≥150 mg/L.5

This information has been provided by Cayman Chemical

References

1. Okumura, N., Yoshida, H., Nishimura, Y., et al. Terpinolene, a component of herbal sage, downregulates AKT1 expression in K562 cells. Oncol. Lett. 3(2), 321-324 (2012).
2. Ramos, E.H., Moraes, M.M., Nerys, L.L., et al. Chemical composition, leishmanicidal and cytotoxic activities of the essential oils from Mangifera indica L. var. Rosa and Espada. Biomed. Res. Int. 2014:734946, (2014).
3. Turkez, H., Aydın, E., Geyikoglu, F., et al. Genotoxic and oxidative damage potentials in human lymphocytes after exposure to terpinolene in vitro. Cytotechnology 67(3), 409-418 (2015).
4. Elzinga, S., Fischedick, J., Podkolinski, R., et al. Cannabinoids and terpenes as chemotaxonomic markers in Cannabis. Nat. Prod. Chem. Res. 3(4), 181 (2015).
5. Ross, S.A., and ElSohly, M.A. The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J. Nat. Prod. 59(1), 49-51 (1996).

String Representations

InChiKey (Click to copy)
MOYAFQVGZZPNRA-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
SMILES (Click to copy)
C1(CC/C(/CC=1)=C(\C)/C)C

Other Databases

KEGG ID
C06075
HMDB ID
HMDB0036994
CHEBI ID
9457
PubChem CID
11463
Cayman ID
21712
PDB ID
9LR

Calculated Physicochemical Properties

Heavy Atoms 10
Rings 1
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 163.92
Topological Polar Surface Area 0.00
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
logP 3.45
Molar Refractivity 45.98

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Updated at
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