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NOOTKATONE

NOOTKATONE Structure
NOOTKATONE structure
CAS No.
4674-50-4
Chemical Name:
NOOTKATONE
Synonyms
NONANOL;（+）-Nootkatone;(4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one;FEMA 3166;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;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-;NOOTKATONE
CBNumber:
CB3751288
Molecular Formula:
C15H22O
Molecular Weight:
218.33
MDL Number:
MFCD00036591
MOL File:
4674-50-4.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 01:14:55
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NOOTKATONE Properties

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
FLAVIS Number 07.089 | 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
biological source synthetic
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.
Major Application flavors and fragrances
Cosmetics Ingredients Functions FRAGRANCE
PERFUMING
InChI 1S/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
InChIKey WTOYNNBCKUYIKC-UHFFFAOYSA-N
SMILES C[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C
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)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P280
Safety Statements  23-24/25
WGK Germany  2
TSCA  TSCA listed
HS Code  29142990
Storage Class 11 - Combustible Solids
Hazard Classifications Skin Sens. 1
Hazardous Substances Data 4674-50-4(Hazardous Substances Data)
REACH Registrations Active
NFPA 704
0
0 0

NOOTKATONE price More Price(73)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W316620 Nootkatone ≥98%, FG 4674-50-4 1 each $101 2026-04-30 Buy
Sigma-Aldrich W316620 Nootkatone ≥98%, FG 4674-50-4 25g $353 2026-04-30 Buy
Sigma-Aldrich W316620 Nootkatone ≥98%, FG 4674-50-4 100g $1150 2026-04-30 Buy
Sigma-Aldrich 74437 (+)-Nootkatone ≥99.0% (GC) 4674-50-4 1g $175 2026-04-30 Buy
Sigma-Aldrich W316620 Nootkatone ≥98%, FG 4674-50-4 1 unit $98.8 2025-07-31 Buy
Product number Packaging Price Buy
W316620 1 each $101 Buy
W316620 25g $353 Buy
W316620 100g $1150 Buy
74437 1g $175 Buy
W316620 1 unit $98.8 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 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.

Synthesis

2(3H)-Naphthalenone, 6-(1-chloro-1-methylethyl)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-, (4R,4aS,6R)-

72453-44-2

NOOTKATONE

4674-50-4

General procedure for the synthesis of nootkatone (compound 9) from compound (CAS: 72453-44-2): sodium acetate trihydrate (0.22 g, 1.6 mmol) was added to a single necked round bottomed flask equipped with a reflux condenser. Chloroenone compound 8 (0.14 g, 0.54 mmol) was dissolved in glacial acetic acid (4 mL) and the solution was injected into the flask. The mixture was heated to 100 °C and kept at this temperature for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into cold water and extracted with chloroform. The organic layer was washed sequentially with 2% aqueous KOH solution, 2N HCl, NaHCO3 solution and brine and then dried with MgSO4. Excess solvent was removed by rotary evaporator to give Nootkatone as a yellow oil in 93% yield. The total yield of pathway b (from β-pinene to Nootkatone) was 23% and that of pathway a was 25%, both showing higher yields. The enantiomeric purity of the final product was almost unchanged from that of the starting material, β-pinene, due to the fact that both the Oxy-Cope reaction and the methylation step preserve the enantiomeric purity. Qualitative analysis showed that the aroma of the synthesized Nootkatone was consistent with that of Nootkatone from other sources. Its 1H NMR data (250 MHz, CDCl3) were in agreement with literature reports: δ 5.77 (s, 1H), 4.75-4.72 (m, 2H), 2.62-2.43 (m, 1H), 2.41-2.22 (m, 4H), 2.09-1.87 (m, 3H), 1.46-1.38 (m, 1H), 1.12- 1.10 (m, 4H), 0.98 (d, 3H). In addition, the use of quaternary ammonium compounds, polyethylene glycol (PEG), or tris[2-(2-methoxyethoxy)ethyl]amine, etc., instead of 18-crown-6 as phase transfer catalysts or metal chelating agents, may be considered in the Oxy-Cope reaction to reduce the cost.

References

[1] Patent: US7112700, 2006, B1. Location in patent: Page/Page column 7; 1/3
[2] Organic Letters, 2009, vol. 11, # 16, p. 3530 - 3533
[3] Patent: WO2017/100437, 2017, A1. Location in patent: Paragraph 00034; 00035
[4] Journal of Organic Chemistry, 1982, vol. 47, # 24, p. 4622 - 4626

NOOTKATONE synthesis

38651-65-9
4674-50-4
Synthesis of NOOTKATONE from (1R)-(+)-NOPINONE

NOOTKATONE Preparation Products And Raw materials

Raw materials

Valencene tert-Butyl chromate 2(3H)-Naphthalenone, 6-(1-chloro-1-methylethyl)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-, (4R,4aS,6R)- Eremophilene Semicarbazide hydrochloride
Sodium acetate Acetic acid

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Preparation Products

(1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene (4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one

NOOTKATONE Suppliers

Global Suppliers ( 397)
Supplier Tel Email Country ProdList Advantage
Hubei Soren Technology Co., Ltd 13419562052 13419562052 wwmlyb@163.com China 4245 58
Originchem Co., Ltd 0523-0523-86200346 15996028822 1583458435@qq.com China 79 58
Hubei Guanzhongtong Technology Co.,LTD 0716-7227299 13507251920 finecq@163.com China 34 58
Apeloa Pharmaceutical Co., Ltd. +86-0571-87635730 +86-13588737631 inquiry@hengdian-group.com China 178 58
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51389 80
Suzhou Jieruisi Biotechnology Co., Ltd 15962550037 1584847559@qq.com China 193 58
Jinan Shengbang Biotechnology Co., Ltd. 13685312009 418162321@qq.com China 60 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Chembest Research Laboratories Limited 021-20908456 sales@BioChemBest.com China 5996 61
Alfa Aesar 400-6106006 saleschina@alfa-asia.com China 30103 84
Supplier Advantage
Hubei Soren Technology Co., Ltd 58
Originchem Co., Ltd 58
Hubei Guanzhongtong Technology Co.,LTD 58
Apeloa Pharmaceutical Co., Ltd. 58
Sigma-Aldrich 80
Suzhou Jieruisi Biotechnology Co., Ltd 58
Jinan Shengbang Biotechnology Co., Ltd. 58
J & K SCIENTIFIC LTD. 76
Chembest Research Laboratories Limited 61
Alfa Aesar 84

View Latest Price from NOOTKATONE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
nootkatone pictures 2026-09-17 nootkatone
4674-50-4
 $1.00 100g 98% 200kg/month WUHAN FORTUNA CHEMICAL CO., LTD
Nootkatone pictures 2026-08-25 Nootkatone
4674-50-4
 $3.00-9.00 99% ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Nootkatone pictures 2026-08-09 Nootkatone
4674-50-4
 96.1%HPLC 2000kgs Chongqing Zhihe Biopharmaceutical Co., Ltd.
  • nootkatone pictures
  • nootkatone
    4674-50-4
  • $1.00
  • 98%
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Nootkatone pictures
  • Nootkatone
    4674-50-4
  • $3.00-9.00
  • 99%
  • ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
  • Nootkatone pictures
  • Nootkatone
    4674-50-4
  • 96.1%HPLC
  • Chongqing Zhihe Biopharmaceutical Co., Ltd.

NOOTKATONE Spectrum

NOOTKATONE(4674-50-4)MSNOOTKATONE(4674-50-4)1HNMR

4674-50-4 (NOOTKATONE) Related Search:

Heptanophenone (+)-NOOTKATONE Dihydro cuminyl alcohol Ethanol Triethylaluminum
Edible essence 1,6-Octadiene NOOTKATONE 3,5-Dimethyl-2-cyclohexen-1-one VALENCENE
NOOTKATONE(SG) Vinylcyclohexane 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%

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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 (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 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> （+）-Nootkatone NOOTKATONE USP/EP/BP NOOTKATONE EX VALENCENE98%/86%/60% nootkartone (+)-Nootkatone, crystalline, 98+% V(+)-Nootkatone Nootkatone 98% NKXAP9800 Nootkatone in methanol Nootkatone, 10 mM in DMSO 4,4a,5,6,7,8-hexahydro-(4R,4a-S,6R)-4,4a-dimethyl-6-(1-methyleneyl)-2(3H)-naphthaleneone (+)-Nootkatone, crystalline (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one FEMA 3166 (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one 4674-50-4 Chiral Building Blocks Asymmetric Synthesis Ketones Organic Building Blocks Chiral Building Blocks Ketones Organic Building Blocks