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ChemicalBook >> CAS DataBase List >>NOOTKATONE

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;Nootkatane
CBNumber:
CB3751288
Molecular Formula:
C15H22O
Molecular Weight:
218.33
MDL Number:
MFCD00036591
MOL File:
4674-50-4.mol
MSDS File:
SDS
Last updated:2025-01-27 09:38:02

NOOTKATONE Properties

Melting point 35-39 °C
Boiling point 125°C 0,5mm
Density 0,997 g/cm3
FEMA 3166 | NOOTKATONE
refractive index n20/D 1.52
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
biological source synthetic
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
Substances Added to Food (formerly EAFUS) NOOTKATONE
EWG's Food Scores 1-2
FDA UNII IZ2Y119N4J
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)
UNSPSC Code 12352205
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P280
Safety Statements  23-24/25
WGK Germany  2
TSCA  Yes
HS Code  29142990
Hazardous Substances Data 4674-50-4(Hazardous Substances Data)
NFPA 704
0
0 0

NOOTKATONE price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W316620 Nootkatone ≥98%, FG 4674-50-4 25g $332 2024-03-01 Buy
Sigma-Aldrich W316620 Nootkatone ≥98%, FG 4674-50-4 100g $1080 2024-03-01 Buy
Sigma-Aldrich 74437 (+)-Nootkatone ≥99.0% (GC) 4674-50-4 1g $160 2024-03-01 Buy
Sigma-Aldrich 44889 (+)-Nootkatone analytical standard 4674-50-4 50mg $111 2022-05-15 Buy
TCI Chemical N0920 (+)-Nootkatone >97.0%(GC) 4674-50-4 1g $54 2024-03-01 Buy
Product number Packaging Price Buy
W316620 25g $332 Buy
W316620 100g $1080 Buy
74437 1g $160 Buy
44889 50mg $111 Buy
N0920 1g $54 Buy

NOOTKATONE Chemical Properties,Uses,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 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.

Chemical Properties

viscous yellow liquid or crystals with a citrus odour;

Chemical Properties

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

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.

38651-65-9
4674-50-4
Synthesis of NOOTKATONE from (1R)-(+)-NOPINONE
Global( 324)Suppliers
Supplier Tel Email Country ProdList Advantage
Chongqing Zhihe Biopharmaceutical Co., Ltd.
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Hebei Chuanghai Biotechnology Co., Ltd 		+86-15531157085 +86-15531157085 abby@chuanghaibio.com China 8807 58
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Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28172 58

View Lastest Price from NOOTKATONE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
NOOTKATONE pictures 2025-03-21 NOOTKATONE
4674-50-4
 US $0.00 / KG 1KG 99% 50000KG/month Hebei Mujin Biotechnology Co.,Ltd
Nootkatone pictures 2025-03-21 Nootkatone
4674-50-4
 US $50.00 / kg 1kg 99 5000 Hebei Zhuanglai Chemical Trading Co Ltd
Nootkatone pictures 2025-03-20 Nootkatone
4674-50-4
 US $0.00-0.00 / kg 0.10000000149011612kg 96.1%HPLC 2000kgs Chongqing Zhihe Biopharmaceutical Co., Ltd.
  • NOOTKATONE pictures
  • NOOTKATONE
    4674-50-4
  • US $0.00 / KG
  • 99%
  • Hebei Mujin Biotechnology Co.,Ltd
  • Nootkatone pictures
  • Nootkatone
    4674-50-4
  • US $50.00 / kg
  • 99
  • Hebei Zhuanglai Chemical Trading Co Ltd
  • Nootkatone pictures
  • Nootkatone
    4674-50-4
  • US $0.00-0.00 / kg
  • 96.1%HPLC
  • Chongqing Zhihe Biopharmaceutical Co., Ltd.

NOOTKATONE Spectrum

(+)-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-55/60% NOOTKATONE WITH GC FEMA 3166 (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)]- 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 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 NOOTKATONE 65-70% NOOTKATONE (+)-Nootkatone> NOOTKATONE USP/EP/BP NOOTKATONE EX VALENCENE98%/86%/60% (+)-Nootkatone, crystalline, 98+% NOOTKATONE, NATURAL (4R)-4,4a,5,6,7,8-Hexahydro-4,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one NONANOL (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one nootkartone 4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- （+）-Nootkatone V(+)-Nootkatone Nootkatone 98% NKXAP9800 Nootkatone in methanol Nootkatone, 10 mM in DMSO 4674-50-4 Chiral Building Blocks Asymmetric Synthesis Ketones Organic Building Blocks Chiral Building Blocks Ketones Organic Building Blocks