4630-07-3

Basic information

• Product Name: VALENCENE
• Synonyms: 7beta,8aalpha)]-theta-(1alph;Valencen;(3R,4AS,5R)-3-ISOPROPENYL-4A,5-DIMETHYL-1,2,3,4,4A,5,6,7-OCTAHYDRO-NAPHTHALENE;(3R,4AS,5R)-4A,5-DIMETHYL-3-ISOPROPENYL-1,2,3,4,4A,5,6,7-OCTAHYDRONAPHTHALENE;FEMA 3443;(+)-VALENCENE;VALENCENE;VALENCENE 85
• CAS NO: 4630-07-3
• Molecular Formula: C₁₅H₂₆
• Molecular Weight: 204.35
• EINECS: 225-047-6
• Product Categories: Plant Oils, Toxins, Phenolic Acids & Derivatives
• Mol File: 4630-07-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 274 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.92 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• BRN: 3539153
• CAS DataBase Reference: VALENCENE(CAS DataBase Reference)
• NIST Chemistry Reference: VALENCENE(4630-07-3)
• EPA Substance Registry System: VALENCENE(4630-07-3)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4630-07-3(Hazardous Substances Data)

Usage

Description

(+)-Valencene is a sesquiterpene that has been found in C. sativa and is an aromatic component of orange essence oil. (+)-Valencene (50 μM) induces heme oxgenase-1 (HO-1) expression in macrophages and inhibits the expression of inducible nitric oxide synthase (iNOS), the production of nitric oxide (NO), and the release of high-mobility group box-1 (HMGB1) in RAW 264.7 cells stimulated with LPS. It also increases the survival rate in a mouse model of sepsis induced by cecal ligation and puncture. (+)-Valencene has been used in the synthesis of nootkatone .

Chemical Properties

clear colorless to yellowish liquid

Occurrence

Reported found in citrus fruits, orange peel, orange juice, bitter orange peel oil, lemon peel oil, grapefruit juice, grapefruit peel oil, kumquat peel oil, leaves and stalk of celery, clove stem, Thymus vulgaris L., fresh mango, globe artichoke, cardamom, mangosteen and cocoa.

Uses

Different sources of media describe the Uses of 4630-07-3 differently. You can refer to the following data:
1. Valencene is a sesquiterpene and an essential oil component found in a variety of plants, and has been shown to have functional antioxidant, antiradical and antimicrobial properties.
2. (+)-Valencene can be used as a precursor to prepare: (+)-Nootkatone (a sesquiterpene) by dark singlet oxygenation. Benzoyloxyvalencene by reacting with tert-butyl peroxy benzoate via Kharasch?Sosnovsky allylic oxidation method. (+)-Lineariifolianone, a natural product.

Definition

ChEBI: A carbobicyclic compound and sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene which is substituted a prop-1-en-2-yl group at position 3 and by methyl groups at positions 4a and 5 (the 3R,4aS,5R diastereoisomer).

Preparation

By a Wolf–Kishner reduction of nootkatone.

General Description

Valencene is the major sesquiterpene aroma constituent of orange peel oil. It is mainly used as a starting material to synthesize nootkatone, an important flavor compound of grapefruit.

InChI:InChI=1/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3

Upstream product

• 10219-75-7 valencene 
• 20489-45-6 11-hydroxy-4α,5α,7β-eremophil-1(10)-ene 
• 17334-55-3 β-gurjunene 
• 372-97-4 farnesyl pyrophosphate 
• 10219-71-3 racemic eremoligenol 

Downstream Products

• 4674-50-4 (+)-nootkatone 
• 136918-14-4 phthalimide 
• 840474-83-1 4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol 
• 35945-71-2 (3R,4aS,5R)-3-isopropyl-4a,5-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene 
• 68384-22-5 2-acetoxyvalencene 
• 1574569-06-4 2-phenylacetoxyvalencene 
• 1574569-05-3 2-(4-methoxybenzoyloxy)valencene 
• 1574569-04-2 2-(4-chlorobenzoyloxy)valencene 
• 71-43-2 benzene 
• 91-20-3 naphthalene 
• 129-00-0 pyrene 
• 95-13-6 1-indene 
• 1207842-45-2 C₂₂H₂₈O₂ 
• 50763-67-2 4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol 

Relevant articles and documents

Late-Stage Intermolecular Allylic C-H Amination

Allylic amination enables late-stage functionalization of natural products where allylic C-H bonds are abundant and introduction of nitrogen may alter biological profiles. Despite advances, intermolecular allylic amination remains a challenging problem due to reactivity and selectivity issues that often mandate excess substrate, furnish product mixtures, and render important classes of olefins (for example, functionalized cyclic) not viable substrates. Here we report that a sustainable manganese perchlorophthalocyanine catalyst, [MnIII(ClPc)], achieves selective, preparative intermolecular allylic C-H amination of 32 cyclic and linear compounds, including ones housing basic amines and competing sites for allylic, ethereal, and benzylic amination. Mechanistic studies support that the high selectivity of [MnIII(ClPc)] may be attributed to its electrophilic, bulky nature and stepwise amination mechanism. Late-stage amination is demonstrated on five distinct classes of natural products, generally with >20:1 site-, regio-, and diastereoselectivity.

Mechanism-Based Post-Translational Modification and Inactivation in Terpene Synthases

Terpenes are ubiquitous natural chemicals with diverse biological functions spanning all three domains of life. In specialized metabolism, the active sites of terpene synthases (TPSs) evolve in shape and reactivity to direct the biosynthesis of a myriad of chemotypes for organismal fitness. As most terpene biosynthesis mechanistically involves highly reactive carbocationic intermediates, the protein surfaces catalyzing these cascade reactions possess reactive regions possibly prone to premature carbocation capture and potentially enzyme inactivation. Here, we show using proteomic and X-ray crystallographic analyses that cationic intermediates undergo capture by conserved active site residues leading to inhibitory self-alkylation. Moreover, the level of cation-mediated inactivation increases with mutation of the active site, upon changes in the size and structure of isoprenoid diphosphate substrates, and alongside increases in reaction temperatures. TPSs that individually synthesize multiple products are less prone to self-alkylation then TPSs possessing relatively high product specificity. In total, the results presented suggest that mechanism-based alkylation represents an overlooked mechanistic pressure during the evolution of cation-derived terpene biosynthesis.

Structure and absolute configuration of kusunol.

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