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watermelon ketone

Watermelon ketone is a fragrance chemical known for its intense melon, marine, and ozone odors, widely used in perfumery as a key scent ingredient.
Chemical Structure

General Material Description

Watermelon ketone, chemically designated as 8-methyl-1,5-benzodioxepin-3-one, is an organic compound with the molecular formula C10H10O3. It is also known under various synonyms such as 7-methyl-2H-1,5-benzodioxepin-3(4H)-one or Calone. The compound exhibits a pale appearance in pure form and is characterized by a distinct melon-like odor combined with aquatic, marine, and ozone aroma impression. Derived originally through synthetic organic chemistry routes, watermelon ketone is primarily utilized as a fragrance material. Its olfactory profile makes it a valuable component in modern perfumery, where it contributes fresh, green, and watery notes. This compound is available commercially typically diluted in solvents such as dipropylene glycol to facilitate handling and blending.

Occurrence, Applicability & Potential Uses

Watermelon ketone is not naturally occurring but is synthetically produced for commercial use due to its unique olfactory qualities. It is widely applied as a fragrance agent in perfumes and personal care products, where it imparts a fresh, watery melon aroma with marine and ozone nuances. Its inclusion enhances the impression of clean, green, and aquatic accords. The compound’s use is recognized and regulated under IFRA (Global) standards, which recommend limiting its concentration in fragrance concentrates to 0.5%. Given its stable aroma and substantivity exceeding 600 hours at 10% in dipropylene glycol, watermelon ketone is favored in fine fragrances, colognes, and various scented formulations aiming for freshness and aquatic themes.

Physico-Chemical Properties Summary

Watermelon ketone is a low-volatility solid with a melting point range between 38 and 41°C at atmospheric pressure. Its vapor pressure at 25°C is very low, around 0.001 mmHg, indicating limited evaporation under typical ambient conditions. The compound demonstrates moderate lipophilicity with a logP value near 2.43, suggesting balanced solubility in both aqueous and organic environments. Soluble in alcohol and dipropylene glycol, it is only slightly soluble in water, with an estimated solubility of approximately 471.5 mg/L at 25°C, and insoluble in paraffin oil. It exhibits good stability across various product matrices such as fine fragrances and detergents, maintaining integrity at usage concentrations around 0.5%. The flash point is approximately 332°F (167°C), supporting safe handling under recommended storage conditions in sealed containers protected from heat and light.

FAQ

What is watermelon ketone and how is it used in fragrances?
Watermelon ketone is a synthetic fragrance compound known for its strong melon-like scent with additional marine and ozone nuances. Chemically identified as 8-methyl-1,5-benzodioxepin-3-one, it serves as a key ingredient in many modern perfumery compositions to impart fresh, green, and watery notes. Due to its intense odor and stability, it is incorporated primarily in fragrance concentrates, colognes, and related cosmetic products.
Where does watermelon ketone occur naturally and what are its key properties?
Watermelon ketone is not found in nature but is manufactured synthetically to meet fragrance industry demands. Physicochemically, it melts between 38 and 41°C and has a low vapor pressure, contributing to its fragrance persistence. It is soluble in several solvents including alcohol and dipropylene glycol but has limited water solubility. These properties support its use in various formulations where stable, fresh aquatic notes are desired.
What safety regulations and standards apply to watermelon ketone in perfumery?
Watermelon ketone is regulated under IFRA (International Fragrance Association) standards, which recommend a maximum concentration of 0.5% in fragrance concentrates to ensure safety. It is classified as an irritant, with hazard statements indicating potential skin and eye irritation. Appropriate handling includes avoiding ingestion and using protective measures such as gloves and eye protection. Regulatory details are documented by agencies including ECHA (EU) and RIFM (US), and safety assessments support its controlled use in fragrances.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

8-methyl-1,5-benzodioxepin-3-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:28940-11-6
Pubchem (cid):120101
Pubchem (sid):135077863
Publications by PubMed
Marine fragrance chemistry.
Characterization and semiquantitative analysis of volatiles in seedless watermelon varieties using solid-phase microextraction.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2934.90.0000
ChemSpider:View
Wikipedia:View

General Material Information

Preferred name watermelon ketone
Trivial Name 7-Methyl-2H-1,5-benzodioxepin-3(4H)-one
Short Description 8-methyl-1,5-benzodioxepin-3-one
Formula C10 H10 O3
CAS Number 28940-11-6
Deleted CAS Number 35783-05-2
ECHA Number 249-320-4
FDA UNII 0NQ136C313
Nikkaji Number J286.485A
MDL MFCD07371373
xLogP3-AA 1.90 (est)
NMR Predictor External link
Synonyms
  • 2H-1,5-benzodioxepin-3(4H)-one, 7-methyl-
  • 7-methyl-1,5-benzodioxepan-3-one
  • 7-methyl-2H-1,5-benzodioxepin-3(4H)-one
  • 7-methyl-2h-benzo-1,5-dioxepin-3(4h)-one
  • 7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one
  • 7-methyl-2H,4H-1,5-benzodioxepin-3-one
  • 7-methyl-2H,4H-benzo[b]1,4-dioxepan-3-one
  • 7-methyl-3,4-dihydro-2H-1,5-benzdioxepine-3-one
  • 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
  • 7-methyl-3,4-dihydro(2H)-1,5-benzodioxepepin-3-one
  • 8-methyl-1,5-benzodioxepin-3-one
  • aquamor (IFF)
  • calone (Firmenich)
  • calone 161 (Firmenich)
  • calone 161 DPG (Firmenich)
  • calone 1951 (Firmenich)
  • ganone
  • marinone (A.C.S. International)
  • methyl benzodioxepinone
  • methyl-7-3,4-dihydro-(2H)-1,5-benzodioxepine-3-one
  • oceanone
  • oceone
  • ozonor
  • watermelon ketone 10% dpg
  • watermelon ketone 50% solution in ethyl diglycol
  • watermelon ketone,calone
  • watermelon ketone (calone)
  • Calone 1951
  • Calone
  • 7-Methyl-1,5-benzodioxepin-3-one

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 178.18730163574
Melting Point 38 to 41°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 166.67 °C TCC
logP (o/w) 2.43
Shelf life 36 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
dipropylene glycol Yes
water, slightly soluble in hot water Yes
water, 471.5 mg/L @ 25 °C (est) Yes
paraffin oil No
Stability
APC: traces - 0.5% Unspecified
candle: traces - 0.5% Unspecified
detergent: traces - 0.5% Unspecified
fine fragrances: traces - 0.5% Unspecified
shampoo: traces - 0.5% Unspecified
shower gel: traces - 0.5% Unspecified
soap: traces - 0.5% Unspecified
softener: traces - 0.5% Unspecified

Organoleptic Properties

Odor Type: Melon
fresh, watery, clean, melon, green, marine, ozone, phenolic
Odor strength high , recommend smelling in a 10.00 % solution or less
Substantivity > 600 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (1986) At 10.00 % in dipropylene glycol. fresh watery clean melon green marine ozone phenolic
The ingredient is very trendy and has been widely used since the 1990’s. The ingredient is the basis of several perfumes. This unusual odorant has intense ozone and marine notes with floral overtones
General comment Marine moss ozone floral heliotrope melon green fresh
The classic fresh, watery, marine note used in many modern compositions, here in an easier to use liquid form originally made available by Firmenich – it’s at 50% in DME (carbitol) – but the material for sale here is a generic equivalent. Fresh, watery, clean, melon-green, marine, ozone

Safety Information

Safety information

European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-rat LD50 1556 mg/kg
Dispose of contents/ container to an approved waste disposal plant.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for watermelon ketone usage levels up to:
0.5000 % in the fragrance concentrate.
Recommendation for watermelon ketone flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):28940-11-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :120101
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
8-methyl-1,5-benzodioxepin-3-one
Chemidplus:0028940116