6753-98-6

Basic information

• Product Name: ALPHA-CARYOPHYLLENE
• Synonyms: α-Caryophyllene, trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene;(E,E,E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene;C09684;α-Humulene,α-Caryophyllene, trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene;alpha-HuMulene >=96.0% (GC);TRANS,TRANS,TRANS-2,6,6,9-TETRAMETHYL-1,4,8-CYCLOUNDECATRIENE;2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene;6,9-tetramethyl-1,4,8-cycloundecatriene(e,e,e)-6
• CAS NO: 6753-98-6
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 229-816-7
• Product Categories: Biochemistry;Terpenes;Terpenes (Others)
• Mol File: 6753-98-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 166-168 °C(lit.)
• Flash Point: 90°C
• Appearance: /
• Density: 0.889 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00812mmHg at 25°C
• Refractive Index: n20/D 1.503(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• Merck: 14,4753
• BRN: 3240075
• CAS DataBase Reference: ALPHA-CARYOPHYLLENE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-CARYOPHYLLENE(6753-98-6)
• EPA Substance Registry System: ALPHA-CARYOPHYLLENE(6753-98-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: GZ4817500
• F: 10-23
• Hazardous Substances Data: 6753-98-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6753-98-6 differently. You can refer to the following data:
1. α-Humulene can be used in the formation of secondary organic aerosol by oxidation.
2. α-Humulene has been used as a reference standard for the determination of isomers of α-humulene in copaiba oleoresin species by high performance liquid chromatography method using the Box-Behnken design.

Definition

ChEBI: The (1E,4E,8E)-isomer of alpha-humulene.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 3675, 1993 DOI: 10.1016/S0040-4039(00)79198-2

General Description

α-Humulene is a class of sesquiterpenes found in Cordia verbenacea essential oil.

InChI:InChI=1/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10-

Upstream product

• 65563-96-4 1,2-epithiohumulene 
• 60545-11-1 2S*,3S*,6S*,7S*,9S*,10S*-humulene 2,3;6,7;9,10-triepoxide 
• 83637-43-8 3,3,7-trinethyl-11-oxo-4E,7E-dodecadienal 
• 90544-15-3 (5E,9E)-11-Bromo-3,3,6,10-tetramethyl-undeca-5,9-dien-1-yne 
• 90544-14-2 (5E,9E)-11-chloro-3,3,5,9-tetramethylundeca-5,9-dien-1-yne 
• 372-97-4 farnesyl pyrophosphate 
• 87-44-5 β-caryophyllene 
• 79898-62-7 5,5-dimethoxy-3,3-dimethyl-1-pentyne 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 78-79-5 isoprene 
• 88941-10-0 (2E,6E,9E)-1-(1-Ethoxy-ethoxy)-2,5,5,9-tetramethyl-cycloundeca-2,6,9-trienecarbonitrile 
• 88941-10-0 (2Z,6E,9E)-1-(1-Ethoxy-ethoxy)-2,5,5,9-tetramethyl-cycloundeca-2,6,9-trienecarbonitrile 
• 88941-09-7 (3E,7E,10E)-12-Chloro-2-(1-ethoxy-ethoxy)-3,6,6,10-tetramethyl-dodeca-3,7,10-trienenitrile 
• 88941-09-7 (3Z,7E,10E)-12-Chloro-2-(1-ethoxy-ethoxy)-3,6,6,10-tetramethyl-dodeca-3,7,10-trienenitrile 

Downstream Products

• 19888-33-6 humulene 2,3-epoxide 
• 19888-34-7 humulene-1,2-monoepoxide 
• 116-04-1 β-humulene 
• 19888-05-2 Humulenon-II 
• 882187-46-4 (3E,7E)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene 
• 831227-95-3 (-)-humulene epoxide II 
• 19888-34-7 [1R-(1R*,3E,7E,11R*)]-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene 
• 108101-44-6 (1S,2S)-1,2-epoxyhumulene 
• 625-34-3 3-oxobutyraldehyde 
• 626-96-0 4-oxopentanal 
• 139255-13-3 2,2-dimethylsuccinaldehyde 

Relevant articles and documents

SYNTHESIS OF NEW HUMULENE DERIVATIVES; (2E,6E,9E)- AND (2Z,6E,9E)-CYCLOUNDECATRIENONES, BY INTRAMOLECULAR ALKYLATION OF PROTECTED CYANOHYDRIN. A ROUTE TO HUMULENE.

Synthesis of (3E,6E,9E)-2,5,5,9-tetramethyl-2,6,9-cycloundecatrienone (4) and (2Z,6E,9E)-2,5,5,9-tetramethyl-2,6,9-cycloundecatrienone (16) based on the intramolecular alkylation of protected cyanohydrin and conversion of the (E,E,E)-trienone 4 to humulene (3) are presented.

An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma

The skeletons of some classes of terpenoids are unusual in that they contain a larger number of Me groups (or their biosynthetic equivalents such as olefinic methylene groups, hydroxymethyl groups, aldehydes, or carboxylic acids and their derivatives) than provided by their oligoprenyl diphosphate precursor. This is sometimes the result of an oxidative ring-opening reaction at a terpene-cyclase-derived molecule containing the regular number of Me group equivalents, as observed for picrotoxan sesquiterpenes. In this study a sesquiterpene cyclase from Trichoderma spp. is described that can convert farnesyl diphosphate (FPP) directly via a remarkable skeletal rearrangement into trichobrasilenol, a new brasilane sesquiterpene with one additional Me group equivalent compared to FPP. A mechanistic hypothesis for the formation of the brasilane skeleton is supported by extensive isotopic labelling studies.

STEREOSPECIFIC SYNTHESIS OF HUMULENE BY TITANIUM-INDUCED DICARBONYL COUPLING

An efficient stereospecific synthesis of humulene was accomplished using titanium-induced cyclization of 3,3,7-trimethyl-11-oxoundeca-4E,7E-dienal as the key step.

Monoepoxidation of humulene 2,3-epoxide to humulene 2,3;6,7-diepoxides. Observation of the rotation of the double bond plane by 1H NMR spectral analysis and conformation

The reaction of (6E,9E)-humulene 2,3-epoxide (7) with m-CPBA produced two known humulene 2,3;6,7-diepoxides (8 and 9), and careful analysis of the 1H NMR of 7 at various temperatures suggested an equilibrium of four possible conformations, CT,