Structure Database (LMSD)

Common Name
(+)-Limonene
Systematic Name
Synonyms
LM ID
LMPR0102090013
Formula
Exact Mass
Calculate m/z
136.1252
Status
Curated



Classification

Biological Context

(+)-Limonene is a monoterpene that has been found in citrus oils and Cannabis and has diverse biological activities.1,2,3,4 It is active against S. aureus, B. cereus, E. faecalis, E. coli, P. aeruginosa, K. pneumoniae, M. catarrhalis, and C. neoformans (MICs = 3-27 mg/ml).1 In a human BGC-823 gastric cancer nude mouse orthotopic transplantation model, (+)-limonene inhibits tumor growth by 47.6% and reduces the number of metastases in the liver, peritoneum, and other organs when administered by gastric perfusion at a dose of 15 ml/kg.5 Dietary administration of (+)-limonene (5 and 10% in chow) reverses doxorubicin-induced decreases in glutathione (GSH) levels in rat kidney.3 (+)-Limonene is toxic to cockroaches and house flies (LD50s = 700 and 90 µg/insect, respectively).6 Formulations containing (+)-limonene have been used as flavoring and fragrance agents, in the treatment of gallstones, heartburn, and gastroesophageal reflux disorder, as well as in the control of insects and algae.

This information has been provided by Cayman Chemical

References

2. Sun, J. D-Limonene: Safety and clinical applications. Altern. Med. Rev. 12(3), 259-264 (2007).
3. van Vuuren, S.F., and Viljoen, A.M. Antimicrobial activity of limonene enantiomers and 1,8-cineole alone and in combination. Flavor and Frag. J. 22(6), 540-544 (2007).
4. Rehman, M.U., Tahir, M., Khan, A.Q., et al. D-limonene suppresses doxorubicin-induced oxidative stress and inflammation via repression of COX-2, iNOS, and NFκB in kidneys of Wistar rats. Exp. Biol. Med. (Maywood) 239(4), 465-476 (2014).
5.  Handbook of Cannabis therapeutics from bench to bedside. (2010).
6. Karr, J.R., and Coats, J.R. Insecticidal properties of d-limonene. J. Pesticide Sci. 12(2), 287-290 (1988).

String Representations

InChiKey (Click to copy)
XMGQYMWWDOXHJM-JTQLQIEISA-N
InChi (Click to copy)
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
SMILES (Click to copy)
C1C[C@H](CC=C1C)C(C)=C

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 10
Rings 1
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 163.92
Topological Polar Surface Area 0.00
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
logP 3.31
Molar Refractivity 45.91

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Updated at
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