A tricyclic sesquiterpene with diverse biological activities
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(+)-Longifolene

Item No. 37362

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,3aR,4S,8aS)-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
CAS Number
475-20-7
Synonyms
  • Junipene
  • Kuromatsuene
  • NSC 150808
Molecular Formula
C15H24
Formula Weight
204.4
Purity
≥90%
Formulation (Request formulation change)
A liquid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 25 mg/ml
SMILES
[H][C@]12[C@@H](C([C@](C)3CCCC2(C)C)=C)CC[C@@]31[H]
InChi Code
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
InChi Key
PDSNLYSELAIEBU-GUIRCDHDSA-N
Origin
Plant/Pinus massoniana Lamb
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

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    1 g

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    Product Description

    (+)-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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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).