beta-Elemene supplier | CasNO.515-13-9

Name
BETA-ELEMENE 82%
EINECS
CAS No. 515-13-9
Article Data25
CAS DataBase
Density 0.862 g/cm³
Solubility
Melting Point
Formula C₁₅H₂₄
Boiling Point 252.1 °C at 760 mmHg
Molecular Weight 204.356
Flash Point 98.3 °C
Transport Information
Appearance
Safety
Risk Codes 66
Molecular Structure
Hazard Symbols
Synonyms Cyclohexane,1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, [1S-(1a,2b,4b)]-;Cyclohexane, 2,4-diisopropenyl-1-methyl-1-vinyl-,(1S,2S,4R)-(-)- (8CI);b-Elemene (6CI);(-)-b-Elemene;Levo-b-elemene;b-Elemene, (-)-;
PSA 0.00000
LogP 4.74720

Synthetic route

: 28028-64-0
(R)-(+)-germacrene A

: 515-13-9
β-elemene

Conditions

Conditions	Yield
In toluene for 2h; Cope rearrangement; Heating;	100%
Cope rearrangement; Heating;

: 873691-52-2
C19H33N2O2P

: 515-13-9
β-elemene

Conditions

Conditions	Yield
Stage #1: C19H33N2O2P With ammonia; lithium In tetrahydrofuran; tert-Amyl alcohol at -33℃; for 10h; Stage #2: With ammonium chloride In tetrahydrofuran; pentanes; tert-Amyl alcohol; water; isoprene	95%

: (5S,7R,8R,10S)-elema-1,3,11-trien-8-ol

: 515-13-9
β-elemene

Conditions

Conditions	Yield
Stage #1: (5S,7R,8R,10S)-elema-1,3,11-trien-8-ol With carbon disulfide; sodium hydride; methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Barton-McCombie deoxygenation; Stage #2: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene; mineral oil for 0.25h; Barton-McCombie deoxygenation; Inert atmosphere; Reflux;	64%

: 639-99-6
elemol

: 515-13-9
β-elemene

Conditions

Conditions	Yield
With pyridine; trichlorophosphate
With pyridine; acetic anhydride

: 83426-07-7
(1S)-1r-methyl-4c-(α-benzoyloxy-isopropyl)-1-vinyl-2c-isopropenyl-cyclohexane

: 515-13-9
β-elemene

Conditions

Conditions	Yield
With N,N-dimethyl-aniline

: C22H30N2O2S

: 515-13-9
β-elemene

Conditions

Conditions	Yield
With sodium tetrahydroborate

O-<4-nitro-benzoyl>-elemol: O-<4-nitro-benzoyl>-elemol

: 515-13-9
β-elemene

Conditions

Conditions	Yield
Pyrolysis;

O-benzoyl-elemol: O-benzoyl-elemol

: 515-13-9
β-elemene

Conditions

Conditions	Yield
Pyrolysis;

: 28028-64-0
(R)-(+)-germacrene A

A: 515-13-9
β-elemene

B: (1R,2R,4R)-2,4-Diisopropenyl-1-methyl-1-vinyl-cyclohexane

Conditions

Conditions	Yield
Cope rearrangement; Heating;

: 28028-64-0
(R)-(+)-germacrene A

A: 515-13-9
β-elemene

B: (1S,2R,4R)-(-)-2,4-diisopropenyl-1-methyl-1-vinyl-cyclohexane

Conditions

Conditions	Yield
at 200℃; Cope rearrangement;

: (+)-1,5-dimethyl-8-(1-methylethenyl)cyclodeca-1E,5Z-diene

A: (-)-cis-β-elemene

B: 515-13-9
β-elemene

C: (1S,2R,4R)-(-)-2,4-diisopropenyl-1-methyl-1-vinyl-cyclohexane

Conditions

Conditions	Yield
at 390℃; Cope rearrangement;

...Expand

: 38655-85-5
(-)-β-elemene-6-one

: 515-13-9
β-elemene

Conditions

Conditions	Yield
With hydrazine Wolff-Kishner Reduction; Heating / reflux;
With potassium hydroxide Wolff-Kishner Reduction; Heating / reflux;

: (-)-beta-elemene-3-one

: 515-13-9
β-elemene

: 4-benzoylbenzylphosphonic ((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl phosphoric) anhydride diammonium salt

: 515-13-9
β-elemene

Conditions

Conditions	Yield
With Nostoc sp. strain PCC7120 sesquiterpene synthase at 25℃; for 18h; aq. buffer; Enzymatic reaction;

: 6902-91-6
germacrone

: 515-13-9
β-elemene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bis(benzonitrile)palladium(II) dichloride / toluene / 1 h / Reflux; Inert atmosphere 2.1: pyridine; potassium tert-butylate / 0.08 h / Inert atmosphere; Reflux 2.2: 0 - 20 °C / Inert atmosphere 3.1: carbon disulfide; sodium hydride; methyl iodide / tetrahydrofuran; mineral oil / 0 - 20 °C 3.2: 0.25 h / Inert atmosphere; Reflux View Scheme

: 20303-60-0
(4S)-trans-β-elemenone

: 515-13-9
β-elemene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; potassium tert-butylate / 0.08 h / Inert atmosphere; Reflux 1.2: 0 - 20 °C / Inert atmosphere 2.1: carbon disulfide; sodium hydride; methyl iodide / tetrahydrofuran; mineral oil / 0 - 20 °C 2.2: 0.25 h / Inert atmosphere; Reflux View Scheme

: 14814-09-6
3-Mercaptopropyltriethoxysilane

: 515-13-9
β-elemene

: C42H90O9S3Si3

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 3h; Inert atmosphere;	88%

: 515-13-9
β-elemene

: 127-09-3
sodium acetate

: 65018-04-4
(-)-elema-1,3,11(13)-trien-12-ol

Conditions

Conditions	Yield
Stage #1: β-elemene With sodium hypochlorite; acetic acid In dichloromethane for 6h; Cooling with ice; Stage #2: sodium acetate In dichloromethane; N,N-dimethyl-formamide at 120℃; for 7h; Further stages;	62%

: 515-13-9
β-elemene

: 913701-50-5
13,14-dichloro-β-elemene

Conditions

Conditions	Yield
With sodium hypochlorite; acetic acid In water at 5 - 20℃; for 5h;	54.6%
With sodium hypochlorite; tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran; dichloromethane; water at 0℃; for 6h;	37%

: 515-13-9
β-elemene

: 885691-35-0
monochloro β-elemene

Conditions

Conditions	Yield
With sodium hypochlorite; acetic acid In dichloromethane	52%
With sodium hypochlorite; acetic acid In dichloromethane at 5℃; for 4.25h;	46.2%
With sodium hypochlorite; acetic acid
With sodium hypochlorite; acetic acid at 20℃; for 6h; Cooling with ice;
With sodium hypochlorite In acetic acid at 0 - 20℃; for 6h;

: 515-13-9
β-elemene

: 13-bromo-β-elemene

Conditions

Conditions	Yield
With N-bromophthalimide; cerium(III) chloride heptahydrate; acetic acid at 10 - 15℃; for 8h; Reagent/catalyst; Cooling with ice;	36.6%
Multi-step reaction with 2 steps 1.1: acetic acid; sodium hypochlorite / dichloromethane / 6 h / 0 - 5 °C 1.2: 8 h / 120 °C 1.3: 2 h / Reflux 2.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 0.17 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hypochlorite; acetic acid / dichloromethane / 4 h / Cooling with ice 1.2: 7 h / 100 °C 1.3: 2 h / Reflux 2.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 0.17 h / 20 °C View Scheme

: 515-13-9
β-elemene

A: 13-bromo-β-elemene

B: C15H22Br2

C: C15H23Br

Conditions

Conditions	Yield
With N-Bromosuccinimide; chloro-trimethyl-silane; ytterbium(III) triflate In tetrahydrofuran; dichloromethane for 8.5h; Cooling with ice;	A n/a B 18.6% C n/a

...Expand

: 515-13-9
β-elemene

: 65018-04-4
(-)-elema-1,3,11(13)-trien-12-ol

Conditions

Conditions	Yield
Stage #1: β-elemene With sodium hypochlorite; acetic acid In dichloromethane for 4h; Cooling with ice; Stage #2: With sodium acetate In N,N-dimethyl-formamide at 100℃; for 7h; Stage #3: With potassium hydroxide In methanol; chloroform for 2h; Reflux;	15%
(i) AcOOH, (ii) LiNEt2; Multistep reaction;
With chicory; enzymes from roots of Cichorium intybus L; NADPH In ethanol for 1h; pH=7.5; Product distribution; Further Variations:; Reagents;
Multi-step reaction with 3 steps 1: sodium hypochlorite / acetic acid / 6 h / 0 - 20 °C 2: potassium iodide / dichloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide / 12 h / 95 °C 3: sodium hydroxide; water View Scheme
Multi-step reaction with 3 steps 1: sodium hypochlorite; acetic acid / dichloromethane 2: N,N-dimethyl-formamide 3: potassium hydroxide / chloroform; methanol View Scheme

: 515-13-9
β-elemene

: C15H24Br2

Conditions

Conditions	Yield
With bromine; acetic acid In acetonitrile at 10 - 28℃; for 5h; Reagent/catalyst; Solvent; Cooling with ice;	11.1%

: 515-13-9
β-elemene

: 515-12-8
(1R)-1r-ethyl-2t,4t-diisopropyl-1-methyl-cyclohexane

Conditions

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

: 515-13-9
β-elemene

: 51297-53-1
1-((1R,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone

Conditions

Conditions	Yield
(i) AcOOH, (ii) HIO4*2H2O; Multistep reaction;

: 515-13-9
β-elemene

A: 51297-53-1
1-((1R,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone

B: 51297-52-0
1-((1S,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone

Conditions

Conditions	Yield
(i) AcOOH, (ii) HIO4*2H2O; Multistep reaction;

: 515-13-9
β-elemene

A: 51297-56-4
1-((1R,2S,5R)-5-Acetyl-2-methyl-2-vinyl-cyclohexyl)-ethanone

B: 1-((1S,2R,5R)-5-Acetyl-2-methyl-2-vinyl-cyclohexyl)-ethanone

Conditions

Conditions	Yield
(i) AcOOH, (ii) HIO4*2H2O; Multistep reaction;

: 515-13-9
β-elemene

A: 65018-04-4
2-((1S,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-prop-2-en-1-ol

B: 65018-04-4
(-)-elema-1,3,11(13)-trien-12-ol

Conditions

Conditions	Yield
(i) AcOOH, (ii) LiNEt2; Multistep reaction;

: 515-13-9
β-elemene

: 24887-73-8
Elemantriol-(2,3,12)

Conditions

Conditions	Yield
(i) NaBH4, BF3-Et2O, THF, (MeOCH2CH2)2O, (ii) H2O2, aq. KOH; Multistep reaction;

: 515-13-9
β-elemene

: C23H38N2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54.6 percent / sodium hypochlorite; acetic acid / H2O / 5 h / 5 - 20 °C 2: 75.1 percent / triethylamine / dimethylformamide / Heating View Scheme

: 515-13-9
β-elemene

: C23H38N2O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54.6 percent / sodium hypochlorite; acetic acid / H2O / 5 h / 5 - 20 °C 2: 68.7 percent / triethylamine / dimethylformamide / Heating View Scheme

: 515-13-9
β-elemene

: C25H42N2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54.6 percent / sodium hypochlorite; acetic acid / H2O / 5 h / 5 - 20 °C 2: 78.2 percent / triethylamine / dimethylformamide / Heating View Scheme

: 515-13-9
β-elemene

: [2-(2-methyl-5-{1-[(2-thiophen-2-yl-ethylamino)-methyl]-vinyl}-2-vinyl-cyclohexyl)-allyl]-(2-thiophen-2-yl-ethyl)-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54.6 percent / sodium hypochlorite; acetic acid / H2O / 5 h / 5 - 20 °C 2: 46.2 percent / triethylamine / dimethylformamide / Heating View Scheme

beta-Elemene Specification

The CAS registry number of Cyclohexane,1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1S,2S,4R)- is 515-13-9. The systematic name is (1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexane. In addition, the molecular formula is C₁₅H₂₄ and the molecular weight is 204.35. It is a natural product and belongs to the class of Drug/Therapeutic Agent. And it should be stored in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 6.63; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.63; (4)ACD/LogD (pH 7.4): 6.63; (5)ACD/BCF (pH 5.5): 64233.09; (6)ACD/BCF (pH 7.4): 64233.09; (7)ACD/KOC (pH 5.5): 96155.7; (8)ACD/KOC (pH 7.4): 96155.7; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.501; (11)Molar Refractivity: 69.81 cm³; (12)Molar Volume: 236.7 cm³; (13)Polarizability: 27.67 ×10^-24cm³; (14)Surface Tension: 29.8 dyne/cm; (15)Density: 0.862 g/cm³; (16)Flash Point: 98.3 °C; (17)Enthalpy of Vaporization: 46.97 kJ/mol; (18)Boiling Point: 252.1 °C at 760 mmHg; (19)Vapour Pressure: 0.0313 mmHg at 25°C.

Preparation of Cyclohexane,1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1S,2S,4R)-: it can be prepared by methyl-triphenyl-phosphonium; iodide and 4-acetyl-2-isopropenyl-1-methyl-cyclohexanecarbaldehyde. This reaction will need reagent n-BuLi and solvents tetrahydrofuran and hexane. The reaction has two steps. The reaction temperature of the first step is -78-20 °C. And the reaction temperature of the second step also is -78-20 °C. Moreover, the reaction time is 40 minutes. The yield is about 89%.

Cyclohexane,1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1S,2S,4R)- can be prepared by methyl-triphenyl-phosphonium; iodide and 4-acetyl-2-isopropenyl-1-methyl-cyclohexanecarbaldehyde.

You can still convert the following datas into molecular structure:
(1)SMILES: C(=C)(\[C@H]1[C@@](\C=C)(C)CC[C@@H](\C(=C)C)C1)C
(2)InChI: InChI=1/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1
(3)InChIKey: OPFTUNCRGUEPRZ-QLFBSQMIBT

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	279mg/kg (279mg/kg)	Zhongyao Tongbao. Bulletin of Chinese Materia Medica. Vol. 6(6), Pg. 32, 1981.
mouse	LD50	intravenous	270mg/kg (270mg/kg)	Zhongguo Zhongliu Linchang. Chinese Journal of Clinical Oncology. Vol. 23, Pg. 453, 1996.
mouse	LD50	oral	> 5gm/kg (5000mg/kg)	Zhongguo Zhongliu Linchang. Chinese Journal of Clinical Oncology. Vol. 23, Pg. 453, 1996.

Product Name

BETA-ELEMENE 82%

Synthetic route

beta-Elemene Specification

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