ChemicalBook > CAS DataBase List > NOOTKATONE

NOOTKATONE

Product Name
NOOTKATONE
CAS No.
4674-50-4
Chemical Name
NOOTKATONE
Synonyms
NONANOL;（+）-Nootkatone;nootkartone;NOOTKATONE, NATURAL;4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one;(4R)-4,4a,5,6,7,8-Hexahydro-4,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one;(4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-;FEMA 3166;NOOTKATONE
CBNumber
CB3751288
Molecular Formula
C15H22O
Formula Weight
218.33
MOL File
4674-50-4.mol
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NOOTKATONE Property

Melting point:
35-39 °C
Boiling point:
125°C 0,5mm
Density 
0,997 g/cm3
refractive index 
n20/D 1.52
FEMA 
3166 | NOOTKATONE
Flash point:
99°C
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
form 
Solid
color 
White to Pale Yellow
Odor
at 100.00 %. grapefruit peel citrus gardenia woody
Odor Type
citrus
optical activity
[α]20/D +182.0±5.0°, c = 1% in ethanol
Water Solubility 
Slightly soluble in ethanol and chloroform. Partly soluble in water.
JECFA Number
1398
BRN 
4676969
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
WTOYNNBCKUYIKC-UHFFFAOYSA-N
LogP
3.84
EPA Substance Registry System
2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- (4674-50-4)
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Safety

Safety Statements 
23-24/25
WGK Germany 
2
TSCA 
Yes
HS Code 
29142990
Hazardous Substances Data
4674-50-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W316620
Product name
Nootkatone
Purity
≥98%, FG
Packaging
25g
Price
$332
Updated
2024/03/01
Sigma-Aldrich
Product number
W316620
Product name
Nootkatone
Purity
≥98%, FG
Packaging
100g
Price
$1080
Updated
2024/03/01
Sigma-Aldrich
Product number
74437
Product name
(+)-Nootkatone
Purity
≥99.0% (GC)
Packaging
1g
Price
$160
Updated
2024/03/01
Sigma-Aldrich
Product number
44889
Product name
(+)-Nootkatone
Purity
analytical standard
Packaging
50mg
Price
$111
Updated
2022/05/15
TCI Chemical
Product number
N0920
Product name
(+)-Nootkatone
Purity
>97.0%(GC)
Packaging
1g
Price
$54
Updated
2024/03/01
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NOOTKATONE Chemical Properties,Usage,Production

Description

Nootkatone has a pleasant taste. It may be prepared by oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.

Description

(+)-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

Nootkatone has a powerful fruity sweet, citrusy, grapefruit peel oil-like aroma.

Chemical Properties

viscous yellow liquid or crystals with a citrus odour;

Chemical Properties

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.

NOOTKATONE Preparation Products And Raw materials

Raw materials

Valencene tert-Butyl chromate

Preparation Products

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View Lastest Price from NOOTKATONE manufacturers

Hangzhou Lin'an tianhong biotechnology co.,ltd.
Product
Nootkatone 4674-50-4
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
50kgs
Release date
2024-12-25
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Nootkatone 4674-50-4
Price
US $50.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-12-13
Chongqing Zhihe Biopharmaceutical Co., Ltd.
Product
Nootkatone 4674-50-4
Price
US $0.00-0.00/kg
Min. Order
0.10000000149011612kg
Purity
96.1%HPLC
Supply Ability
2000kgs
Release date
2024-08-22

4674-50-4, NOOTKATONERelated Search:

DIHYDRO CUMINYL ALCOHOL (+)-NOOTKATONE Triethylaluminum Ethanol HEPTANOPHENONE Edible essence VINYLCYCLOHEXANE NOOTKATONE 3,5-Dimethyl-2-cyclohexen-1-one VALENCENE NOOTKATONE(SG) 1,6-Octadiene 2,6-DIMETHYL-1,6-HEPTADIENE NOOTKATONE50% (-)-nootkatone,5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one NOOTKATONE(SECONDARY STANDARD) NOOTKATONE81% NOOTKATONE97%

  • NOOTKATONE
  • (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
  • 2(3h)-naphthalenone,
  • 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4alpha,4aalpha,6beta)]-
  • 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-,[4R-(4.alpha.,4a.alpha.,6.beta.)]-
  • 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-,[4R-(4.alpha.,4a.alpha.,6.beta.)]-2(3H)-Naphthalenone
  • NOOTKATONE 98% CRYSTALS
  • NOOTKATONE DISTILLED 50%
  • NOOTKATONE EX-CITRUS 70% NATURAL
  • NOOTKATONE, NATURAL
  • NOOTKATONE-55/60%
  • NOOTKATONE WITH GC
  • FEMA 3166
  • (4R)-4,4a,5,6,7,8-Hexahydro-4,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one
  • (4R)-4,4a,5,6,7,8-Hexahydro-4β,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one
  • (4R)-4,4a,5,6,7,8-Hexahydro-6α-isopropenyl-4β,4aβ-dimethylnaphthalene-2(3H)-one
  • (4R)-4β,4aβ-Dimethyl-6α-isopropenyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-one
  • Zinc05225089
  • (+)-Nootkatone >=99.0% (GC)
  • 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3h)-naphthalenon
  • 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4alpha,4aalpha,6beta)]-
  • 4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one
  • 4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone,[4R-(4.alpha.,4a.alpha.4
  • 4aalpha,6beta)]-[4theta-(4alph
  • 4betaH,5alpha-Eremophila-1(10),11-dien-2-one
  • 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one
  • 6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
  • Nootkatane
  • [4R-(4alpha,4aalpha,6beta)]-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one
  • (+)-NOOTKATONE, CRYSTALLINE, 98+%
  • 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-
  • (+)-nootkatone, crystalline
  • 4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE
  • (4R-(4alpha,4aalpha,6beta))-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalin-2(3H)-on
  • NONANOL
  • NOOTKATONE 65-70%
  • (+)-Nootkatone&gt
  • （+）-Nootkatone
  • NOOTKATONE USP/EP/BP
  • NOOTKATONE EX VALENCENE98%/86%/60%
  • (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
  • nootkartone
  • (+)-Nootkatone, crystalline, 98+%
  • V(+)-Nootkatone
  • Nootkatone 98% NKXAP9800
  • Nootkatone in methanol
  • 4674-50-4
  • Chiral Building Blocks
  • Asymmetric Synthesis
  • Ketones
  • Organic Building Blocks
  • Chiral Building Blocks
  • Ketones
  • Organic Building Blocks