53111-25-4

Basic information

• Product Name: (1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene
• Synonyms: (1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene;(-)-2,4aβ,5,6,7,9aβ-Hexahydro-3,5,5,9-tetramethyl-1H-benzocycloheptene;[4aS,(-)]-2,4aβ,5,6,7,9aβ-Hexahydro-3,5,5,9-tetramethyl-1H-benzocycloheptene;gamma-himachalene
• CAS NO: 53111-25-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• Mol File: 53111-25-4.mol

Chemical Properties

• Boiling Point: 267.8°Cat760mmHg
• Flash Point: 104.6°C
• Appearance: /
• Density: 0.861g/cm³
• Vapor Pressure: 0.0132mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: (1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene(53111-25-4)
• EPA Substance Registry System: (1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene(53111-25-4)

Safety Data

• Hazardous Substances Data: 53111-25-4(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
(1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene is used as a fragrance ingredient for its woody, floral, and musky scent. It is particularly valued in the manufacturing of perfumes and scented products due to its unique aroma profile and ability to enhance the longevity and intensity of other fragrance components.
Used in Organic Synthesis:
(1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene is utilized as a key intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications. Its unique structure and properties make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Research:
Due to its distinctive bicyclic structure and chemical properties, (1R,7R)-2,6,6,9-tetramethylbicyclo[5.4.0]undeca-2,8-diene serves as an important subject of study in chemical research. It contributes to the understanding of molecular interactions, reaction mechanisms, and the development of new synthetic methodologies, further expanding its potential applications across various industries.

InChI:InChI=1/C15H24/c1-11-7-8-13-12(2)6-5-9-15(3,4)14(13)10-11/h6,10,13-14H,5,7-9H2,1-4H3/t13-,14-/m0/s1

Upstream product

• 40716-68-5 (2-cis,6-trans)-farnesyl diphosphate 

Relevant articles and documents

Alternate Cyclization Cascade Initiated by Substrate Isomer in Multiproduct Terpene Synthase from Medicago truncatula

Promiscuity of terpene synthases results in the enormous diversity of terpenes found in nature. Multiproduct sesquiterpene synthase MtTPS5 isolated from Medicago truncatula generates 27 optically pure products from its natural substrate (2E,6E)-farnesyl diphosphate (FDP). In order to study the promiscuity of MtTPS5, (2Z,6E)-FDP, an analogue of presumptive reaction intermediates from natural reaction cascade, was utilized as a substrate. This stereoisomer induced a novel cyclization pathway leading to sesquiterpenes based on humulane, amorphene, and himachalane skeletons. Interestingly, none of these products matched those observed on incubation of MtTPS5 with natural (2E,6E)-FDP. Further determination of the absolute configuration of each product helped rebuild the stereochemical route of the reaction cascade. Interestingly, the presence of only one enantiomer of each product was observed, indicating the highly stereospecific nature of the enzymatic reaction. Substrate promiscuity of terpene synthases provides organism access to novel chemical bouquets of high optical purity by utilizing existing enzymes. The presence of this mechanism was indicated by the presence of these alternate products in natural herbivore-induced volatiles of M. truncatula.