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Name	(+)-Longifolene	EINECS	207-491-2
CAS No.	475-20-7	Density	0.93 g/cm³
PSA	0.00000	LogP	4.41500
Solubility	7.9mg/L at 24℃	Melting Point	N/A
Formula	C₁₅H₂₄	Boiling Point	252.2 °C at 760 mmHg
Molecular Weight	204.356	Flash Point	102.2 °C
Transport Information	N/A	Appearance	Light-yellowish oil-shaped liquid
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	1,4-Methanoazulene,decahydro-4,8,8-trimethyl-9-methylene-, (1S,3aR,4S,8aS)-(+)- (8CI); 1,4-Methanoazulene,decahydro-4,8,8-trimethyl-9-methylene-, [1S-(1a,3ab,4a,8ab)]-; Longifolene (6CI); (+)-Longifolene; Junipen;Junipene; Kuromatsuen; Kuromatsuene; Longifolen; NSC 150808; d-Longifolene; a-Longifolene	Article Data	14

(+)-Longifolene Synthetic route

: 143-33-9
sodium cyanide

: 4678-06-2, 4678-07-3
[(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]methyl 4-methylbenzenesulfonate

A: 943033-63-4
[(1R,2S,7R,8S,9R)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]acetonitrile

B: 475-20-7
longifolene

Conditions

Conditions	Yield
sodium iodide In dimethyl sulfoxide at 90℃; for 24h;	A 69% B 21%

: 465-24-7, 16846-28-9, 18374-92-0, 27551-75-3, 51897-51-9
(+)-isolongiborneol

: 475-20-7
longifolene

Conditions

Conditions	Yield
With dmap; methanesulfonyl chloride In pyridine at 105℃; for 16h;	66%

: 18367-70-9
(-)-(1R)(2R)(7S)(8R)(9S)-3,3,7-Trimethyl-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>undecane

: 475-20-7
longifolene

Conditions

Conditions	Yield
In benzene at 525℃;	56%

: 99481-28-4
10-keto-longifolene

: 475-20-7
longifolene

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 4h; Heating;	55%

: 82053-87-0
Trimethyl-((1S,3aR,4S,8aS,9S)-4,8,8-trimethyl-decahydro-1,4-methano-azulen-9-ylmethyl)-ammonium; iodide

A: 475-20-7
longifolene

B: 82053-85-8
N,N-Dimethylisolongifolamine

Conditions

Conditions	Yield
With silver(l) oxide 1.) aq. MeOH, 30 deg C, 3 h; 2.) pyrolyse (oil-bath(250 deg C), 40 mm); Yield given. Multistep reaction;	A n/a B 54%
With silver(l) oxide 1.) aq. MeOH, 30 deg C, 3 h; 2.) pyrolyse (oil-bath(250 deg C), 40 mm); Yield given. Multistep reaction;	A 10% B n/a

: 4678-06-2, 4678-07-3
[(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]methyl 4-methylbenzenesulfonate

A: 475-20-7
longifolene

B: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With aluminum oxide In Petroleum ether for 12h;	A 2 g B 9%

: 5989-08-2
(+)-α-Longipinene

A: 1461-03-6
β-himachalene

B: 3853-83-6
α-himachalene

C: 475-20-7
longifolene

D: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 18 - 29℃; for 7h;	A 10 % Chromat. B 46 % Chromat. C 32 % Chromat. D 2 % Chromat.
With boron trifluoride diethyl etherate In diethyl ether at 28 - 29℃; for 7h; Product distribution; other acid, other solvent, other temperature, other time;	A 10 % Chromat. B 46 % Chromat. C 32 % Chromat. D 2 % Chromat.

: 5989-08-2
(+)-α-Longipinene

A: 1461-03-6
β-himachalene

B: 475-20-7
longifolene

C: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With sulfuric acid In acetic acid at 50 - 51℃; for 1h;	A 52 % Chromat. B 4 % Chromat. C 32 % Chromat.

: (1S,3aR,4S,8aR)-4,8,8,9-Tetramethyl-decahydro-1,4-methano-azulen-9-ol

: 475-20-7
longifolene

Conditions

Conditions	Yield
With thionyl chloride In pyridine at 0℃; for 0.166667h; Yield given;

: 3α-Brom-7βH-longifolan

: 475-20-7
longifolene

Conditions

Conditions	Yield
With ethanol at 40 - 60℃; Kinetics;

(+)-Longifolene Chemical Properties

Molecule structure of d-Longifolene (CAS NO.475-20-7):

Molecular Weight: 204.35106 g/mol
Molecular Formula: C₁₅H₂₄
Density: 0.93 g/cm³
Boiling Point: 252.2 °C at 760 mmHg
Flash Point: 102.2 °C
Index of Refraction: 1.508
Molar Refractivity: 64.85 cm³
Molar Volume: 217.4 cm³
Polarizability: 25.71×10^-24 cm³
Surface Tension: 31.2 dyne/cm
Enthalpy of Vaporization: 46.97 kJ/mol
Vapour Pressure: 0.0312 mmHg at 25 °C
Storage Temp.: 2-8 °C
XLogP3-AA: 5.1
Exact Mass: 204.187801
MonoIsotopic Mass: 204.187801
Heavy Atom Count: 15
Complexity: 312
Canonical SMILES: CC1(CCCC2(C3C1C(C2=C)CC3)C)C
InChI: 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
InChIKey: PDSNLYSELAIEBU-UHFFFAOYSA-N
EINECS: 207-491-2
Product Categories of d-Longifolene (CAS NO.475-20-7): Pharmaceutical Raw Materials

(+)-Longifolene Uses

d-Longifolene (475-20-7) is used in the manufacture or preparation of Flavor.

(+)-Longifolene Toxicity Data With Reference

1.		orl-rat LD50:>5 g/kg		FCTOD7 Food and Chemical Toxicology. 30 (1992),67S.
2.		skn-rbt LD50:>5 g/kg		FCTOD7 Food and Chemical Toxicology. 30 (1992),67S.

(+)-Longifolene Consensus Reports

Reported in EPA TSCA Inventory.

(+)-Longifolene Safety Profile

WGK Germany: 2
RTECS: PB7724500
F: 8-10-23
Low toxicity by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

(+)-Longifolene Specification

d-Longifolene (CAS NO.475-20-7) is also named as 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene- ; 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S-(1alpha,3abeta,4alpha,8abeta)) ; Junipen ; Junipene ; Kuromatsuen ; Kuromatsuene ; Longifolen ; Longifolene ; NSC 150808 .

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