Longifolene | CAS#475-20-7 | hydrocarbon

MedKoo Cat#: 596329 | Name: Longifolene

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts. Longifolene is used in organic synthesis for the preparation of dilongifolylborane, a chiral hydroborating agent.

Chemical Structure

Longifolene

CAS#475-20-7

Theoretical Analysis

MedKoo Cat#: 596329

Name: Longifolene

CAS#: 475-20-7

Chemical Formula: C15H24

Exact Mass: 204.1878

Molecular Weight: 204.36

Elemental Analysis: C, 88.16; H, 11.84

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 250.00	2 weeks

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Related CAS #

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Synonym

Longifolene; Junipen; Junipene; Kuromatsuen; Kuromatsuene; Longifolen; NSC 150808; NSC-150808; NSC150808;

IUPAC/Chemical Name

(1S,3aR,4S,8aR)-4,8,8-trimethyl-9-methylenedecahydro-1,4-methanoazulene

InChi Key

PDSNLYSELAIEBU-RGCMKSIDSA-N

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

SMILES Code

C=C1[C@@]2([H])CC[C@@]3([H])[C@]1(C)CCCC(C)(C)[C@]23[H]

Appearance

Liquid

Purity

>75% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits.

In vitro activity:

The obtained outcomes revealed that longifolene possesses cytotoxic potential against both prostate (IC50 = 78.64 µg/mL) as well as oral (IC50 = 88.92 µg/mL) cancer cell lines with the least toxicity in healthy Vero cells (IC50 = 246.3 µg/mL) when compared to doxorubicin. Reference: Molecules. 2022 Sep 6;27(18):5764. https://pubmed.ncbi.nlm.nih.gov/36144491/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	489.34

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 204.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Grover M, Behl T, Virmani T, Sanduja M, Makeen HA, Albratty M, Alhazmi HA, Meraya AM, Bungau SG. Exploration of Cytotoxic Potential of Longifolene/Junipene Isolated from Chrysopogon zizanioides. Molecules. 2022 Sep 6;27(18):5764. doi: 10.3390/molecules27185764. PMID: 36144491; PMCID: PMC9504982.

In vitro protocol:

In vivo protocol:

TBD

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