473-13-2

Basic information

• Product Name: ALPHA-SELINENE
• Synonyms: (-)-α-Serinene;[2R,(-)]-1,2,3,4,4a,5,6,8aβ-Octahydro-4aα,8-dimethyl-2-(1-methylvinyl)naphthalene;1,2,3,4,4a,5,6,8a-Octahydro-4a,8-dimethyl-2-(prop-1-en-2-yl)-naphthalene;3-isopropenyl-5,8a-dimethyl-2,3,4,4a,7,8-hexahydro-1H-naphthalene;5,8a-dimethyl-3-prop-1-en-2-yl-2,3,4,4a,7,8-hexahydro-1H-naphthalene
• CAS NO: 473-13-2
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• Mol File: 473-13-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 270°Cat760mmHg
• Flash Point: 102°C
• Appearance: /
• Density: 0.888g/cm³
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.489
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Slightly), Hexane (Slightly)
• CAS DataBase Reference: ALPHA-SELINENE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-SELINENE(473-13-2)
• EPA Substance Registry System: ALPHA-SELINENE(473-13-2)

Safety Data

• Hazardous Substances Data: 473-13-2(Hazardous Substances Data)

Usage

Uses

α-Selinine, >85% is a natural product found in essential oils from variety of plants. It is a functional antioxidant with antiradical and antimicrobial properties.

Definition

ChEBI: An isomer of selinene where the double bond in the octahydronaphthalene ring system is endocyclic (2R,4aR,8aR)-configuration..

InChI:InChI=1/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,13-14H,1,5,7-10H2,2-4H3

Synthetic route

(-)-3α-chloro-4βH-eudesm-11,12-ene (200343-76-6) → α-selinene (473-13-2)

Conditions	Yield
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide at 138 - 140℃; for 5h;	86%

(R)-(+)-germacrene A (28028-64-0) → 5α,7αH-eudesm-11(13)-en-4α-ol (16641-47-7) + α-cyperene (17627-30-4) + α-selinene (473-13-2) + beta-selinene (17066-67-0)

Conditions	Yield
With silica gel In diethyl ether at 20℃; for 24h;	A 23% B n/a C n/a D n/a

selina-4(15),7(11)-diene (515-17-3, 58893-88-2, 138874-69-8) → α-selinene (473-13-2)

Conditions	Yield
With formic acid

(-)-dihydro-α-cyperol (200343-74-4) → α-selinene (473-13-2)

Conditions	Yield
(i) H3BO3, toluene, (ii) (pyrolysis); Multistep reaction;
Multi-step reaction with 2 steps 1: 88 percent / PPh3-NCS / tetrahydrofuran / 3 h 2: 86 percent / LiBr, Li2CO3 / dimethylformamide / 5 h / 138 - 140 °C View Scheme
Multi-step reaction with 2 steps 1: Py 2: 400 °C View Scheme

Dihydro-α-cyperyl-ethylcarbonat (10064-36-5) → α-selinene (473-13-2)

Conditions	Yield
at 400℃;

2-(4-nitro-benzoyloxy)-2-((1R)-4c-methyl-4t-vinyl-3c-isopropenyl-cyclohexyl-(r))-propane (30824-64-7) → α-selinene (473-13-2)

Conditions	Yield
at 195 - 200℃;

(+)-1-chloro-1.4a-dimethyl-7-<α-chloro-isopropyl>-decalin → α-selinene (473-13-2)

Conditions	Yield
With potassium hydroxide at 30 - 70℃;
With aniline at 100 - 140℃;

(R)-(+)-germacrene A (28028-64-0) → α-cyperene (17627-30-4) + α-selinene (473-13-2) + beta-selinene (17066-67-0)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.116667h;

eudesma-4,11-dien-3-one (473-08-5) → α-selinene (473-13-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / Li, liq.NH3 / diethyl ether / 25 h / -78 °C 2: 92 percent / LAH, t-BuOH / tetrahydrofuran / 18 h / 0 - 20 °C 3: 88 percent / PPh3-NCS / tetrahydrofuran / 3 h 4: 86 percent / LiBr, Li2CO3 / dimethylformamide / 5 h / 138 - 140 °C View Scheme
Multi-step reaction with 2 steps 1: Na, nPrOH 2: (i) H3BO3, toluene, (ii) (pyrolysis) View Scheme
Multi-step reaction with 3 steps 1: Na, nPrOH 2: Py 3: 400 °C View Scheme
Multi-step reaction with 3 steps 1: LiNH2, liq. NH3 / diethyl ether 2: LiAlH4, tBuOH / tetrahydrofuran 3: (i) H3BO3, toluene, (ii) (pyrolysis) View Scheme
Multi-step reaction with 4 steps 1: LiNH2, liq. NH3 / diethyl ether 2: LiAlH4, tBuOH / tetrahydrofuran 3: Py 4: 400 °C View Scheme

(-)-Dihydro-α-cyperone (10064-31-0) → α-selinene (473-13-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / LAH, t-BuOH / tetrahydrofuran / 18 h / 0 - 20 °C 2: 88 percent / PPh3-NCS / tetrahydrofuran / 3 h 3: 86 percent / LiBr, Li2CO3 / dimethylformamide / 5 h / 138 - 140 °C View Scheme
Multi-step reaction with 2 steps 1: LiAlH4, tBuOH / tetrahydrofuran 2: (i) H3BO3, toluene, (ii) (pyrolysis) View Scheme
Multi-step reaction with 3 steps 1: LiAlH4, tBuOH / tetrahydrofuran 2: Py 3: 400 °C View Scheme

α-selinene (473-13-2) + beta-selinene (17066-67-0) → 4α(H)-eudesmane (30824-81-8) + 4β(H)-eudesmane (473-11-0)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

α-selinene (473-13-2) → 2,3,4,4a,5,6-hexahydro-1,4a-dimethyl-7-(1-methylethyl)-naphthalene (28624-23-9, 28624-28-4, 62358-43-4, 473-14-3) + 1.4a-dimethyl-7-isopropyl-1.2.3.4.4a.5-hexahydro-naphthalene (599-57-5)

Conditions	Yield
With sulfuric acid

α-selinene (473-13-2) → 1-methyl-7-isopropylnaphthalene (490-65-3)

Conditions	Yield
at 310 - 315℃; Leiten des Dampfes ueber Platin-Kohle;

α-selinene (473-13-2) → 4α(H)-eudesmane (30824-81-8)

Conditions	Yield
With acetic acid; platinum Hydrogenation;
With ethyl acetate; platinum Hydrogenation;
With hydrogen; platinum(IV) oxide

α-selinene (473-13-2) → 4β(H)-eudesmane (473-11-0)

Conditions	Yield
With hydrogen; platinum(IV) oxide

sulfuric acid (7664-93-9) + α-selinene (473-13-2) → 2,3,4,4a,5,6-hexahydro-1,4a-dimethyl-7-(1-methylethyl)-naphthalene (28624-23-9, 28624-28-4, 62358-43-4, 473-14-3) + η-selinene (?)

α-selinene (473-13-2) + beta-selinene (17066-67-0) → 4β(H)-eudesmane (473-11-0) + eudesmane

Conditions	Yield
With acetic acid; platinum Hydrogenation;

α-selinene (473-13-2) + palladium coal → 1-methyl-7-isopropylnaphthalene (490-65-3) + tetrahydroselinene

Conditions	Yield
at 205℃;

Upstream product

• 515-17-3 selina-4⁽¹⁵⁾,7⁽¹¹⁾-diene 
• 4341-24-6 5-methylcyclohexan-1,3-dione 
• 83093-43-0 (1S,4aS,7R,8aS)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-octahydro-naphthalen-2-one 
• 473-16-5 (+)-α-eudesmol 
• 92803-54-8 C₂₂H₃₄N₂O₄S 
• 92803-57-1 Toluene-4-sulfonic acid 2-((2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-2-hydroxy-propyl ester 
• 80322-01-6 2-((2R,4aR,8aR)-4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-propane-1,2-diol 
• 117212-69-8 3-Isopropenyl-5,8a-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 
• 115562-82-8 3,9-dimethyl-11-(methylethenyl)-1,3,9-decatriene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 78719-76-3 1-((2R,4aR,8aR)-4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-ethanone 
• 138089-74-4 3-ethoxy-5-methyl-6-(3-methyl-2-butenyl)-2-cyclohexen-1-one 
• 138089-76-6 2-(4-ethoxy-6-methyl-2-oxo-3-cyclohexenyl)acetaldehyde 
• 138089-84-6 1,5-dimethyl-8-(1-methylethenyl)-4-(phenylseleno)bicyclo<4.4.0>decan-3-one 

Downstream Products

• 473-11-0 4β(H)-eudesmane 
• 30824-81-8 (+)-Selinan 

Relevant articles and documents

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Germacrenes from fresh costus roots

Four germacrenes, previously shown to be intermediates in sesquiterpene lactone biosynthesis, were isolated from fresh costus roots (Saussurea lappa). The structures of (+)-germacrene A, germacra-1(10),4,11(13)-trien-12-ol, germacra-1(10),4,11(13)-trien-12-al, and germacra-1(10),4,11(13)-trien-12-oic acid were deduced by a combination of spectral data and chemical transformations. Heating of these compounds yields (-)-β-elemene, (-)-elema-1,3,11(13)-trien-12-ol, (-)-elema-1,3,11(13)-trien-12-al, and elema-1,3,11(13)-trien12-oic acid respectively, in addition to small amounts of their diastereomers. Acid induced cyclisation of the germacrenes yields selinene, costol, costal, and costic acid respectively. It is highly probable that the elemenes reported in literature for costus root oil are artefacts.

TOTAL SYNTHESIS OF RACEMIC SELINA-3,7(11)-DIENE, α-SELINENE AND α-EUDESMOL

Three natural products of the eudesmane family, selina-3,7(11)-diene, α-selinene and α-eudesmol, have been synthesized using a common strategy.The key steps involved in the strategy include the direct deprotonation/alkylation of isoprenyl sulfone and the intramolecular Diels-Alder reaction.