Structure Database (LMSD)

Common Name
(+)-longifolene
Systematic Name
(1S,3aR,4S,8aS)-4,8,8-trimethyl-9-methylidenedecahydro-1,4-methanoazulene
Synonyms
  • (+)-Longifolen
  • (1S,3aR,4S,8aS)-(+)-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
  • (1S,3aR,4S,8aS)-4,8,8-trimethyl-9-methylenedecahydro-1,4-methanoazulene
  • Junipen
  • Kuromatsuen
  • Longifolen
  • [1S-(1alpha,3abeta,4alpha,8abeta)]-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
  • d-longifolene
  • junipene
  • kuromatsuene
LM ID
LMPR0103500017
Formula
C15H24
Exact Mass
Calculate m/z
204.1878
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C15 isoprenoids (sesquiterpenes) [PR0103]
Longifolane sesquiterpenoids [PR010350]

Biological Context

(+)-Longifolene is a tricyclic sesquiterpene that has been found in C. japonica and has diverse biological activities.1,2,3,4 It is active against S. aureus and E. faecalis (MICs = 600 and 60 ppm, respectively).1 (+)-Longifolene (1 mg/L) is toxic to red tide plankton (S. costatum).2 It induces cytotoxicity in DU145 prostate cancer and SCC-9 oral squamous cell carcinoma cells (IC50s = 78.64 and 88.92 µg/ml, respectively).3 (+)-Longifolene is toxic to waterfleas (D. magna and C. dubia) and fathead minnows (P. promelas; LC50s = 0.44, 0.41, and 10.2 mg/L, respectively).4

This information has been provided by Cayman Chemical

References

1. Schmidt, E., Bail, S., Friedl, S.M., et al. Antimicrobial activities of single aroma compounds. Nat. Prod. Commun. 5(9), 1365-1368 (2010).
2. Tsuruta, K., Yoshida, Y.M., Kusumoto, N., et al. Inhibition activity of essential oils obtained from Japanese trees against Skeletonema costatum. J. Wood Sci. 57, 520-525 (2011).
3. Grover, M., Behl, T., Virmani, T., et al. Exploration of cytotoxic potential of longifolene/junipene isolated from Chrysopogon zizanioides. Molecules 27(18), 5764 (2022).
4. Sweet, L.I., and Meier, P.G. Lethal and sublethal effects of azulene and longifolene to Microtox®, Ceriodaphnia dubia, Daphnia magna, and Pimephales promelas. Bull. Environ. Contam. Toxicol. 58(2), 268-274 (1997).

String Representations

InChiKey (Click to copy)
PDSNLYSELAIEBU-GUIRCDHDSA-N
InChi (Click to copy)
InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1
SMILES (Click to copy)
C1C[C@]2([H])C(=C)[C@@]3(C)CCCC(C)(C)[C@]2([H])[C@]31[H]

Other Databases

Wikipedia
longifolene
CHEBI ID
49282
PubChem CID
1796220
Cayman ID
37362

Calculated Physicochemical Properties

Heavy Atoms 15
Rings 3
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 228.34
Topological Polar Surface Area 0.00
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
logP 4.42
Molar Refractivity 64.58

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