4674-50-4 Usage
Description
Different sources of media describe the Description of 4674-50-4 differently. You can refer to the following data:
1. Nootkatone has a pleasant taste. It may be prepared by oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.
2. (+)-Nootkatone is sesquiterpene ketone originally isolated from grapefruit juice and peel oil with diverse biological activity. It is lethal against ticks, fleas, and mosquitoes with LC50 values of 0.0029, 0.0061, and 0.0046% w/v, respectively. Pretreatment of wood with (+)-nootkatone reduces tunnel lengths, feeding, and survival rates in C. formosanus termites. (+)-Nootkatone (10-100 μM) dose-dependently activates AMPKα1 and AMPKα2 in C2C12 mouse myoblast lysate containing a substrate peptide. It dose-dependently inhibits platelet aggregation induced by collagen, thrombin , and arachidonic acid when used at concentrations ranging from 10 to 100 μM with almost complete inhibition at the highest concentration. In vivo, (+)-nootkatone (3-30 mg/kg, p.o.) dose-dependently increases the length of tail bleeding time in mice. (+)-Nootkatone (0.1-0.3%, p.o.) dose-dependently reduces body weight and plasma glucose levels in mice fed a high-fat and high-sucrose diet.
Chemical Properties
Different sources of media describe the Chemical Properties of 4674-50-4 differently. You can refer to the following data:
1. Nootkatone has a powerful fruity sweet, citrusy, grapefruit peel oil-like aroma.
2. viscous yellow liquid or crystals with a citrus odour;
3. NOOTKATONE has been isolated from grapefruit peel and juice
and identified in other citrus oils as well. The commercially available product is a
colorless to yellowish liquid with a typical grapefruit odor.
Nootkatone can be prepared by oxidation of valencene, a sesquiterpene hydrocarbon
isolated from orange oils. The oxidation can be accomplished either by
chemical or by biotechnological methods.
Nootkatone is used for flavoring beverages.
Occurrence
Reported found in grapefruit oil and juice; traces are also reported found in the oils of bergamot, lemon, lime,
orange and tangerine; also reported formed in canned orange juice on storage.
Uses
Nootkatone is an effective repellent/insecticide against mosquitos, and may repel bed bugs, head lice and other insects. Nootkatone in spray form has been shown as an effective repellent/insecticide against deer ticks and lone star ticks.
Preparation
By oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.
Definition
ChEBI: A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R
stereoisomer).
Aroma threshold values
Detection: 170 to 800 ppb
Taste threshold values
Taste characteristics at 20 ppm: grapefruit, citrus, orange and butter.
General Description
(+)-nootkatone, a bicyclic conjugated sesquiterpene ketone with a grapefruit-like flavor, is commonly used in fragrance, food, cosmetics and pharmaceutical industry. It can be synthesized from (+)-valencene via biotransformation. (+)-nootkatone is the active ingredient responsible for the antiplatelet effect of Cyperus rotundus, a well-known oriental traditional medicine. It also shows promising efficacy against Staphylococcus aureus biofilms.
Check Digit Verification of cas no
The CAS Registry Mumber 4674-50-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,7 and 4 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4674-50:
(6*4)+(5*6)+(4*7)+(3*4)+(2*5)+(1*0)=104
104 % 10 = 4
So 4674-50-4 is a valid CAS Registry Number.
InChI:InChI=1/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
4674-50-4Relevant articles and documents
Preparation of (-)-aristolochene from (+)-valencene: Absolute configuration of (+)-aristolochene from Aspergillus terreus
Cane,Salaski,Prabhakaran
, p. 1943 - 1944 (1990)
The absolute configuration of (+)-aristolochene (1a), isolated from Aspergillus terreus, has been established by direct comparison with a sample of (-)-aristolochene (1b) prepared from (+)-valencene (2).
Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation
Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori
, p. 1513 - 1514 (2005)
Nootkatone (2), the most important and expensive aromatic of grapefruit, decreases the somatic fat ratio, and thus its demand is increasing in the cosmetic and fiber sectors. A sesquiterpene hydrocarbon, (+)-valencene (1), which is cheaply obtained from Valencia orange, was biotransformed by the green algae Chlorella species and fungi such as Mucor species, Botryosphaeria dothidea, and Botryodiplodia theobromae to afford nootkatone (2) in high yield.
Manganese complex catalyst for valencene oxidation: The first use of metalloporphyrins for the selective production of nootkatone
DeFreitas-Silva, Gilson,Moreira Meireles, Alexandre,Robles-Azocar, Patrícia,da Silva, Vinicius Santos,de Melo, Carla Nunes
, (2021)
This work describes the oxidation of valencene, a sesquiterpene easily obtained from citrus fruits, and responsible for the fresh odor of oranges. The reactions were catalyzed by manganese porphyrins derived from 5,10,15,20-tetrakis(3,5-dimethoxyphenyl)porphyrin (H2T3,5DMPP): [MnIII(T3,5DMPP)Cl] (MnP1) and [MnIII(Br12T3,5DMPP)Cl] (MnP2), using iodosylbenzene (PhIO), iodobenzene diacetate [PhI(OAc)2], and molecular oxygen as oxidants. The systems MnP1/O2/acetonitrile and MnP1/O2/diethyl carbonate led to higher yields of valencene oxidation products (44% and 48%, respectively) as compared with MnP2 (9% and 7%, respectively), with nootkatone being the major product. The addition of a small amount of imidazole (molar MnP1: imidazole ratio of 1:5) to the MnP1/O2/diethyl carbonate led to superior yields (64%) as compared with systems without the additive. A mechanism for the formation of the two products obtained was also proposed.
METHOD FOR THE MANUFACTURE OF α,β-UNSATURATED KETONES
-
Page/Page column 13, (2021/10/30)
A method for the manufacture of an α,β-unsaturated ketone, which method comprises oxidizing an alkene having -CH2- adjacent a carbon-carbon double bond to α,β-unsaturated ketone by passing air or oxygen through a solution of the hydrocarbon containing a catalyst consisting of N-hydroxyphthalimide (NHPI) and cobalt diacetate tetrahydrate at standard temperature and pressure during a period of at least 12 hours.
PROCESS FOR THE PREPARATION OF NOOTKATONE BY USING A IRON (III) PORPHYRIN COMPLEX CATALYST
-
Page/Page column 5-7, (2020/12/29)
An allylic oxidation process comprising: forming a mixture containing valencene and an iron (lll)-X porphyrin complex catalyst in a sustainable solvent, introducing molecular oxygen into the mixture, and effecting allylic oxidation to produce nootkatone.
