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Safety Information

235172

Sigma-Aldrich

(+)-Longifolene

≥98%

Synonym(s):

(1R,2S,7S,9S)-3,3,7-Trimethyl-8-methylenetricyclo[5.4.0.02.9]undecane, Junipene, Kuromatsuene, [1S-(1α,3aβ,4α,8aβ)]-Decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene

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About This Item

Empirical Formula (Hill Notation):
C15H24
CAS Number:
475-20-7
Molecular Weight:
204.35
Beilstein:
2044263
EC Number:
207-491-2
MDL number:
MFCD00082306
UNSPSC Code:
12352103
PubChem Substance ID:
329752427

Assay

≥98%

optical activity

[α]22/D +46°, neat

refractive index

n20/D 1.504 (lit.)

bp

254 °C/706 mmHg (lit.)

density

0.928 g/mL at 25 °C (lit.)

SMILES string

CC1(C)CCC[C@]2(C)C3CCC(C13)C2=C

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-/m0/s1

InChI key

PDSNLYSELAIEBU-WOFVOEOOSA-N

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Signal Word

Danger

Hazard Statements

H304,H317,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

213.8 °F - closed cup

Flash Point(C)

101.00 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
15423AS
10405LR
08331KN
05702AO
04920KG

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Gopal Subramaniam et al.
Magnetic resonance in chemistry : MRC, 44(12), 1118-1121 (2006-09-27)
We describe the conformation and stereospecific 1H and 13C chemical shift assignments of longifolene 1 and its penultimate precursor 2 through the combined use of ab initio calculations and experimental NMR techniques. The predicted stable conformation for both compounds was
Hydroxyisolongifolaldehyde: a new metabolite of (+)-longifolene in rabbits.
T Ishida et al.
Journal of pharmaceutical sciences, 71(8), 965-966 (1982-08-01)
Sasan Karimi et al.
Journal of natural products, 66(4), 520-523 (2003-04-26)
Through a convenient ring expansion reaction of key intermediate 1, enone 5, containing the longifolene skeleton, was produced. Elaboration of 5 via hydrogenation, Wittig reaction, Simmons-Smith reaction, and subsequent hydrogenolysis led to ketone 9. Reductive debromination of 9 afforded 10
Gregory A Ho et al.
The Journal of organic chemistry, 70(13), 5139-5143 (2005-06-18)
W. S. Johnson's total synthesis of the sesquiterpenoid longifolene is a classic example of the power of cationic polycyclizations for constructing complex molecular architectures. Herein we revisit the key polycyclization step of this synthesis using hybrid Hartree-Fock/density functional theory calculations
Julieta Rubio et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 60(9-10), 711-716 (2005-12-03)
Fractionation with n-hexane/ethyl acetate (1:1 v/v) by open column chromatography of the oleoresin from Pinus oocarpa Schiede yielded two diterpenes, pimaric acid (1) and dehydroabietic acid (5), the sesquiterpene longifolene (3) and a diterpenic mixture containing pimaric acid (1), isopimaric
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