515-13-9

Basic information

• Product Name: BETA-ELEMENE 82%
• Synonyms: BETA-ELEMENE 82%;C15 H24, Cyclohexan, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-;levo-beta-Elemene;β-Elemen;(1S,2S,4R)-1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexane;Cyclohexane,1-ethenyl-1-Methyl-2,4-bis(1-Methylethenyl)-, (1S,2S,4R)-;(1S,2S,4R)-(?)-2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane;(-)-beta-Elemene analytical standard
• CAS NO: 515-13-9
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.355
• Product Categories: API
• Mol File: 515-13-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 252℃
• Flash Point: 98℃
• Appearance: /
• Density: 0.862
• Vapor Pressure: 0.0313mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: 2-8°C
• BRN: 2207781
• CAS DataBase Reference: BETA-ELEMENE 82%(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-ELEMENE 82%(515-13-9)
• EPA Substance Registry System: BETA-ELEMENE 82%(515-13-9)

Safety Data

• Statements: 66
• WGK Germany: 3
• RTECS: GU9660000
• Hazardous Substances Data: 515-13-9(Hazardous Substances Data)

Usage

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

Synthetic route

(R)-(+)-germacrene A (28028-64-0) → β-elemene (515-13-9)

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

C19H33N2O2P (873691-52-2) → β-elemene (515-13-9)

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 → β-elemene (515-13-9)

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%

elemol (639-99-6) → β-elemene (515-13-9)

Conditions	Yield
With pyridine; trichlorophosphate
With pyridine; acetic anhydride

(1S)-1r-methyl-4c-(α-benzoyloxy-isopropyl)-1-vinyl-2c-isopropenyl-cyclohexane (83426-07-7) → β-elemene (515-13-9)

Conditions	Yield
With N,N-dimethyl-aniline

C22H30N2O2S → β-elemene (515-13-9)

Conditions	Yield
With sodium tetrahydroborate

O-<4-nitro-benzoyl>-elemol → β-elemene (515-13-9)

Conditions	Yield
Pyrolysis;

O-benzoyl-elemol → β-elemene (515-13-9)

Conditions	Yield
Pyrolysis;

(R)-(+)-germacrene A (28028-64-0) → β-elemene (515-13-9) + (1R,2R,4R)-2,4-Diisopropenyl-1-methyl-1-vinyl-cyclohexane

Conditions	Yield
Cope rearrangement; Heating;

(R)-(+)-germacrene A (28028-64-0) → β-elemene (515-13-9) + (1S,2R,4R)-(-)-2,4-diisopropenyl-1-methyl-1-vinyl-cyclohexane

Conditions	Yield
at 200℃; Cope rearrangement;

(+)-1,5-dimethyl-8-(1-methylethenyl)cyclodeca-1E,5Z-diene → (-)-cis-β-elemene + β-elemene (515-13-9) + (1S,2R,4R)-(-)-2,4-diisopropenyl-1-methyl-1-vinyl-cyclohexane

Conditions	Yield
at 390℃; Cope rearrangement;

(-)-β-elemene-6-one (38655-85-5) → β-elemene (515-13-9)

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

(-)-beta-elemene-3-one → β-elemene (515-13-9)

4-benzoylbenzylphosphonic ((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl phosphoric) anhydride diammonium salt → β-elemene (515-13-9)

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

germacrone (6902-91-6) → β-elemene (515-13-9)

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

(4S)-trans-β-elemenone (20303-60-0) → β-elemene (515-13-9)

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

3-Mercaptopropyltriethoxysilane (14814-09-6) + β-elemene (515-13-9) → C42H90O9S3Si3

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

β-elemene (515-13-9) + sodium acetate (127-09-3) → (-)-elema-1,3,11(13)-trien-12-ol (65018-04-4)

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%

β-elemene (515-13-9) → 13,14-dichloro-β-elemene (913701-50-5)

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%

β-elemene (515-13-9) → monochloro β-elemene (885691-35-0)

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;

β-elemene (515-13-9) → 13-bromo-β-elemene

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

β-elemene (515-13-9) → 13-bromo-β-elemene + C15H22Br2 + C15H23Br

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

β-elemene (515-13-9) → (-)-elema-1,3,11(13)-trien-12-ol (65018-04-4)

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

β-elemene (515-13-9) → C15H24Br2

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

β-elemene (515-13-9) → (1R)-1r-ethyl-2t,4t-diisopropyl-1-methyl-cyclohexane (515-12-8)

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

β-elemene (515-13-9) → 1-((1R,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone (51297-53-1)

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

β-elemene (515-13-9) → 1-((1R,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone (51297-53-1) + 1-((1S,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone (51297-52-0)

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

β-elemene (515-13-9) → 1-((1R,2S,5R)-5-Acetyl-2-methyl-2-vinyl-cyclohexyl)-ethanone (51297-56-4) + 1-((1S,2R,5R)-5-Acetyl-2-methyl-2-vinyl-cyclohexyl)-ethanone

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

β-elemene (515-13-9) → 2-((1S,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-prop-2-en-1-ol (65018-04-4) + (-)-elema-1,3,11(13)-trien-12-ol (65018-04-4)

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

β-elemene (515-13-9) → Elemantriol-(2,3,12) (24887-73-8)

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

β-elemene (515-13-9) → C23H38N2

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

β-elemene (515-13-9) → C23H38N2O2

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

β-elemene (515-13-9) → C25H42N2

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

β-elemene (515-13-9) → [2-(2-methyl-5-{1-[(2-thiophen-2-yl-ethylamino)-methyl]-vinyl}-2-vinyl-cyclohexyl)-allyl]-(2-thiophen-2-yl-ethyl)-amine

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

Upstream product

• 21499-63-8 (2E,8Ξ)-5-isopropenyl-2,8-dimethyl-deca-2,8-diene-1,10-diol 
• 21499-61-6 ethyl (5R*,E)-2-methyl-8-oxo-5-(prop-1-en-2-yl)non-2-enoate 
• 21499-60-5 ethyl 2-methyl-5-isopropenyl-8,8-ethylenedioxy-trans-2-nonenoate 
• 21499-62-7 ethyl 2,8-dimethyl-5-isopropenyl-undeca-trans-2-(trans/cis)-8-diene-1,10-dioate 
• 639-99-6 elemol 
• 83426-07-7 (1S)-1r-methyl-4c-(α-benzoyloxy-isopropyl)-1-vinyl-2c-isopropenyl-cyclohexane 
• 28028-64-0 (R)-(+)-germacrene A 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 100693-10-5 3-Isopropenyl-6-methyl-10-oxo-6E-undecenal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 138-86-3 limonene. 
• 7086-79-5 (3R*)-6-oxo-3-(prop-1-en-2-yl)heptanal 
• 88682-28-4 (5R*)-5-(2-hydroxyethyl)-6-methylhept-6-en-2-one 

Downstream Products

• 515-12-8 (1R)-1r-ethyl-2t,4t-diisopropyl-1-methyl-cyclohexane 
• 1460-98-6 1,3-di-isopropyl-4-methylbenzene 
• 51297-53-1 1-((1R,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone 
• 51297-52-0 1-((1S,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-ethanone 
• 51297-56-4 1-((1R,2S,5R)-5-Acetyl-2-methyl-2-vinyl-cyclohexyl)-ethanone 
• 65018-04-4 2-((1S,3S,4S)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-prop-2-en-1-ol 
• 65018-04-4 (-)-elema-1,3,11⁽¹³⁾-trien-12-ol 
• 24887-73-8 Elemantriol-(2,3,12) 

Relevant articles and documents

Conformational analysis of (+)-germacrene A by variable-temperature NMR and NOE spectroscopy

(+)-Germacrene A, an important intermediate in sesquiterpene biosynthesis, was isolated in pure form from a genetically engineered yeast and was characterized by chromatographic properties (TLC, GC), MS, optical rotation, UV, IR, 1H NMR, and 13C NMR data. Variable-temperature 500 MHz 1H NMR spectra in CDCl3 showed that this flexible cyclodecadiene ring exists as three NMR-distinguishable conformational isomers in a ratio of about 5:3:2 at or below ordinary probe temperature (25 °C). The conformer structures were assigned by 1H NMR data comparisons, NOE experiments, and vicinal couplings as follows: 1a (52%, UU), 1b (29% UD), and 1c (19%, DU).

Sesquiterpenes of the liverwort Scapania undulata

The essential oil of the liverwort Scapania undulata, collected in the Harz mountains, Northern Germany, was analysed by gas chromatography (GC), GC-mass spectrometry (MS) and several new components were isolated and investigated by various NMR techniques. As new natural compounds the sesquiterpene hydrocarbons (+)-helminthogermacrene (1) [the 4Z-isomer of germacrene A (9)], (-)-cis-β-elemene (2) as a Cope-rearrangement product of 1, (+)-β-isolongibornene (3) and (-)-perfora-1,7-diene (4) could be identified. 1 has an identical mass spectrum and identical GC retention time on a non-polar stationary phase as germacrene A (9) but is considerably more stable than the latter. The Cope-rearrangement of 1 proceeds slowly at 350°C and (-)-cis-β-elemene (2) is formed together with small amounts of other diastereoisomers.

Efficient synthesis of the anticancer β-elemene and other bioactive elemanes from sustainable germacrone

Highly efficient preparations of anticancer β-elemene and other bioactive elemanes were carried out using the natural product germacrone as a renewable starting material. The syntheses were achieved in only 3-5 steps with excellent overall yields (43-54%). An enantioselective approach to these molecules is also described

Synthesis of beta-elemene, intermediates thereto, analogues and uses thereof

The present invention provides convergent processes for preparing beta-elemene, and analogues thereof. Also provided are analogues related to beta-elemene and intermediates useful for preparing the same. The present invention further provides novel compositions based on analogues of beta-elemene and methods for the treatment of cancer, such as brain tumor, lung cancer, colorectal cancer, gastric intestional cancer, and stomach cancer.