483-76-1

Basic information

• Product Name: (+)-DELTA-CADINENE
• Synonyms: (1S-cis)-4,7-dimethyl-1,2,3,5,6,8-hexahydro-1-(1-methylethyl)naphthalene;1-Isopropyl-4,7-dimethyl-1,2,3,5,6,8a-hexahydronaphthalene;Cadina-1(10),4-diene;delta-Cadinene;delta-Cadinene, (+)-;Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)-;naphthalene,1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-,(1S-cis)-;C15 H24, fx: Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-
• CAS NO: 483-76-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• Mol File: 483-76-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 277.87°C (rough estimate)
• Flash Point: 38 °C
• Appearance: /
• Density: 0.9160
• Vapor Pressure: 0.00669mmHg at 25°C
• Refractive Index: n20/D 1.509
• CAS DataBase Reference: (+)-DELTA-CADINENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-DELTA-CADINENE(483-76-1)
• EPA Substance Registry System: (+)-DELTA-CADINENE(483-76-1)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 3
• RTECS: EU8900000
• Hazardous Substances Data: 483-76-1(Hazardous Substances Data)

Usage

General Description

(+)-Delta-Cadinene is an organic compound that is classified as a sesquiterpene, which is a class of terpenes that consist of three isoprene units. It is naturally occurring and is found in a wide range of plant species, where it contributes to the plant's aroma and flavor. Additionally, (+)-Delta-Cadinene has been found to exhibit certain biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. However, its toxicity and potential side effects have not been fully investigated, so caution should be taken in its use. It is often used in the perfume and flavour industry due to its distinctive spicy, woody aroma.

InChI:InChI=1/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13,15H,5-8H2,1-4H3/t13-,15-/m0/s1

Upstream product

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Downstream Products

• 39029-41-9 (+)-γ-cadinene 
• 1460-97-5 γ-cadinene 
• 483-77-2 (-)-Calamenene 
• 35943-92-1 (7S,10R)-trans-calamenene 
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• 483-73-8 Tetrahydrocadinen 

Relevant articles and documents

The amino-terminal segment in the β-domain of δ-cadinene synthase is essential for catalysis

Despite its distance from the active site the flexible amino-terminal segment (NTS) in the β-domain of the plant sesquiterpene cyclase δ-cadinene synthase (DCS) is essential for active site closure and desolvation events during catalysis.

Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers

Sesquiterpene synthases catalyze with different catalytic fidelity the cyclization of farnesyl pyrophosphate (FPP) into hundreds of known compounds with diverse structures and stereochemistries. Two sesquiterpene synthases, Cop4 and Cop6, were previously isolated from Coprinus cinereus as part of a fungal genome survey. This study investigates the reaction mechanism and catalytic fidelity of the two enzymes. Cyclization of all-trans-FPP ((E,E)-FPP) was compared to the cyclization of the cis-trans isomer of FPP ((Z,E)-FPP) as a surrogate for the secondary cisoid neryl cation intermediate generated by sesquiterpene synthases, which are capable of isomerizing the C2-C3 π bond of all-trans-FPP. Cop6 is a "high-fidelity" α-cuprenene synthase that retains its fidelity under various conditions tested. Cop4 is a catalytically promiscuous enzyme that cyclizes (E,E)-FPP into multiple products, including (-)-germacrene D and cubebol. Changing the pH of the reaction drastically alters the fidelity of Cop4 and makes it a highly selective enzyme. Cyclization of (Z,E)-FPP by Cop4 and Cop6 yields products that are very different from those obtained with (E,E)-FPP. Conversion of (E,E)-FPP proceeds via a (6R)-β-bisabolyl carbocation in the case of Cop6 and an (E,E)-germacradienyl carbocation in the case of Cop4. However, (Z,E)-FPP is cyclized via a (6S)-β-bisabolene carbocation by both enzymes. Structural modeling suggests that differences in the active site and the loop that covers the active site of the two enzymes might explain their different catalytic fidelities.

8-Hydroxy-(+)-δ-cadinene is a precursor to hemigossypol in Gossypium hirsutum

[3H](+)-δ-Cadinene and its 8-hydroxy derivative, prepared from (1RS)-[1-3H]FPP by the action of one and two recombinant enzymes, respectively, were infiltrated into cotyledons of bacterial blight-resistant cotton plants as they biosynthesized sesquiterpene phytoalexins in response to infection by Xanthomonas campestris pv. malvacearum. Following both treatments, tritium appeared in the HPLC fraction that contained hemigossypol. Hemigossypol was isolated from the cotyledons that had been treated with [3H](+)-8-hydroxy-δ-cadinene and was trimethylsilylated and purified. In two experiments, specific radioactivity of the hemigossypol derivative indicated that 5% and 10%, respectively, of the [3H](+)-8-hydroxy-δ-cadinene had been converted to hemigossypol.