Musk ketone is a synthetic macrocyclic musk fragrance. Its synthesis involves a multi-step process that begins with the condensation of cyclohexanone with 3-methyl-2-butanone to form a key intermediate. This intermediate is then subjected to a series of reactions, including ring closure and oxidation, to yield the final musk ketone product. It is a potent odorant and is used in perfumes and other consumer products. Its effects on human health are controversial, with some studies suggesting potential endocrine disrupting properties, while others find no significant risks. The compound's importance lies in its long-lasting and pleasant fragrance, making it a valuable ingredient in the perfume industry. Research on musk ketone focuses on its synthesis, safety, and potential environmental impact.'
musk ketone: increases activity of glutathione S-transferase and thus may prove to be useful cancer chemoprotectant [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 6669 |
| CHEMBL ID | 1877463 |
| CHEBI ID | 174791 |
| SCHEMBL ID | 113330 |
| MeSH ID | M0098790 |
| Synonym |
|---|
| STK725128 |
| CHEBI:174791 |
| acetophenone, 4'-tert-butyl-2',6'-dimethyl-3',5'-dinitro- |
| ethanone, 1-[4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl]- |
| 2,6-dimethyl-3,5-dinitro-4-tert-butylacetophenone |
| acetophenone,6'-dimethyl-3',5'-dinitro- |
| nsc15339 |
| musk ketone |
| ethanone,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl]- |
| 4'-tert-butyl-2',5'-dinitroacetophenone |
| 81-14-1 |
| nsc-15339 |
| 2-acetyl-5-tert-butyl-4,6-dinitroxylene |
| einecs 201-328-9 |
| 2,6-dimethyl-3,5-dinitro-4-t-butylacetophenone |
| nsc 15339 |
| ethanone, 1-(4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl)- |
| 2,6-dinitro-3,5-dimethyl-4-acetyl-tert-butylbenzene |
| ccris 4677 |
| 4'-tert-butyl-2',6'-dimethyl-3',5'-dinitroacetophenone |
| 1-(4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl)ethanone |
| 4-tert-butyl-3,5-dinitro-2,6-dimethylacetophenone |
| ai3-02440 |
| 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone |
| brn 2062638 |
| musk ketone, >=98% |
| NCGC00164404-01 |
| 1-(4-tert-butyl-2,6-dimethyl-3,5-dinitrophenyl)ethanone |
| ketone moschus, >=97.0% (n) |
| AC-11085 |
| A840051 |
| 1-(4-tert-butyl-2,6-dimethyl-3,5-dinitro-phenyl)ethanone |
| 4-07-00-00808 (beilstein handbook reference) |
| unii-483v3e1l6j |
| 483v3e1l6j , |
| hsdb 7694 |
| dtxsid6025690 , |
| cas-81-14-1 |
| dtxcid405690 |
| NCGC00255386-01 |
| tox21_301627 |
| BBL011671 |
| AKOS005524284 |
| FT-0629036 |
| 1-tert-butyl-3,5-dimethyl-2,6-dinitro-4-acetylbenzene |
| musk ketone [hsdb] |
| musk ketone [inci] |
| 2,6 dimethyl-4-tert-butyl-3,5-dinitroacetophenone |
| 4-tert-butyl-2,6-dimethyl-3,5-dinitroacetophenone |
| 4-aceto-3,5-dimethyl-2,6-dinitro-tert-butylbenzene |
| 3,5-dinitro-4-tert-butyl-2,6-dimethylacetophenone |
| 2,6-dimethyl-3,5-dinitro-4-tert-butyl acetophenone |
| SCHEMBL113330 |
| mfcd00024271 |
| 1-[4-(tert-butyl)-2,6-dimethyl-3,5-dinitrophenyl]ethan-1-one |
| W-104216 |
| CHEMBL1877463 |
| 4-t-butyl-2,6-dimethyl-3,5-dinitroacetophenone |
| 2,6-dinitro-3,5-dimethyl-4-acetyl-tertbutylbenzene |
| WXCMHFPAUCOJIG-UHFFFAOYSA-N |
| 4-tert-butyl-2,6-dimethyl-3,5-dinitroactophenone |
| 1-acetyl-4-tert-butyl-2,6-dimethyl-3,5-dinitrobenzene |
| ketone musk |
| 3,5-dinitro-2,6-dimethyl-4-tert-butyl acetophenone |
| 1-[4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl]ethanone |
| ketone moschus |
| 1-(4-tert-butyl-2,6-dimethyl-3,5-dinitrophenyl)ethanone # |
| 1-(4-tert-butyl-2,6-dimethyl-3,5-dinitrophenyl)ethan-1-one |
| SR-01000324027-1 |
| sr-01000324027 |
| musk ketone 10 microg/ml in cyclohexane |
| ketonmoschus |
| acetyl-dinitro-butyl-xylene |
| 1-[4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl]ethanone, 9ci |
| 4'-tert-butyl-2', 6'-dimethyl-3',5'-dinitroacetophenone |
| 4'-tert-butyl-2',6'-dimethyl-3',5'-dinitro-acetophenone |
| dinitro-tert-butylxylyl methyl ketone |
| musk ketone;3-methylcyclopentadecanone |
| 3',5'-dinitro-2',6'-dimethyl-4'-tert-butylacetophenone |
| Q1948992 |
| FS-4310 |
| AC-34811 |
| CS-0018535 |
| HY-N2045 |
Musk ketone is a widely used artificial fragrance. It has been identified in human fatty tissue and milk.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Musk ketone is a widely used artificial fragrance which has been identified in human fatty tissue and milk. " | ( Musk ketone enhances benzo(a)pyrene induced mutagenicity in human derived Hep G2 cells. Freywald, C; Jenter, C; Knasmüller, S; Mersch-Sundermann, V; Parzefall, W; Schneider, H, 2001) | 3.2 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Based on the results of these studies, none of the four fragrances tested were more toxic in the conceptuses than in the dams." | ( Developmental toxicity studies of four fragrances in rats. Api, AM; Christian, MS; Diener, RM; Hoberman, AM; Parker, RM, 1999) | 0.3 |
| "Through the determinations of wheat (Triticum aestivum) seed germination and seedling growth, the toxic effect of emerging pollutant musk ketone was investigated." | ( [Toxic effect of musk ketone based on the determinations of wheat (Triticum aestivum) seed germination and root elongation]. Fan, F; Wang, ME; Zhou, QX, 2008) | 0.89 |
| "This study aims at developing a method for the determination of 9 synthetic musk compounds in seafood products by combining the quick, easy, cheap, effective, rugged, and safe (QuEChERS) method and determination by gas chromatography mass spectrometry (GC-EI-MS)." | ( Synthetic musk in seafood products from south Europe using a quick, easy, cheap, effective, rugged and safe extraction method. Cavalheiro, J; Lanceleur, L; Monperrus, M; Saraiva, M, 2016) | 0.43 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The percutaneous absorption rate of both chemicals was ∼11%." | ( In vitro determination of transdermal permeation of synthetic musks and estimated dermal uptake through usage of personal care products. Gu, Y; Li, X; Yu, Y; Zhang, X, 2017) | 0.46 |
Male and female mice were dosed with 250, 500 or 1000 mg musk ketone/kg body weight by a single intraperitoneal injection in corn oil. Repeated daily dosing for 14 days resulted in little bioaccumulation for musk xylene and accumulation of about three-fold for musm ketone.
| Excerpt | Relevance | Reference |
|---|---|---|
| " To evaluate the ability of MK to induce cytochromes P450, mice were dosed daily by oral gavage at dosages ranging from 5 to 500 mg/ kg MK for 7 days." | ( Characterization of the effects of musk ketone on mouse hepatic cytochrome P450 enzymes. Caudill, D; Lehman-McKeeman, LD; Stuard, SB, 1997) | 0.57 |
| " Repeated daily dosing for 14 days resulted in little bioaccumulation for musk xylene and accumulation of about three-fold for musk ketone." | ( Dermal absorption and disposition of musk ambrette, musk ketone and musk xylene in rats. Ford, RA; Hawkins, DR, 1999) | 0.76 |
| " Male F344 rats were dosed orally with MX (10, 50 or 200 mg/kg) or MK (20, 100 or 200 mg/kg) for 7 days, after which CYP1A, 2B and 3A enzyme activities and protein levels were determined." | ( Effects of musk xylene and musk ketone on rat hepatic cytochrome P450 enzymes. Caudill, D; Lehman-McKeeman, LD; Madan, A; Parkinson, A; Pearce, RE; Vassallo, JD, 1999) | 0.6 |
| " Male and female mice were dosed with 250, 500 or 1000 mg musk ketone/kg body weight by a single intraperitoneal injection in corn oil." | ( An in vivo mouse micronucleus assay on musk ketone. Api, AM; Gudi, R, 2000) | 0.82 |
| " In this study, kinetics and dose-response assessments of 2-amino-MK (AMK) metabolite, bound to cysteine-hemoglobin (Hb) in rainbow trout, formed by enzymatic nitro-reduction of MK have been demonstrated." | ( Biological transformation, kinetics and dose-response assessments of bound musk ketone hemoglobin adducts in rainbow trout as biomarkers of environmental exposure. Mottaleb, MA; Moy, TW; Zimmerman, JH, 2008) | 0.58 |
| " Biotransformation, dose-response and toxicokinetics studies of 2-amino-MX (2-AMX), 2-amino-MK (2-AMK) and 4-amino-MX (4-AMX) metabolites, covalently bound to cysteine amino acids in proteins in fish liver, formed by enzymatic nitro-reduction of MX and MK, have been described." | ( Identification of bound nitro musk-protein adducts in fish liver by gas chromatography-mass spectrometry: biotransformation, dose-response and toxicokinetics of nitro musk metabolites protein adducts in trout liver as biomarkers of exposure. Islam, MR; Mottaleb, MA; Osemwengie, LI; Sovocool, GW, 2012) | 0.38 |
| Class | Description |
|---|---|
| aromatic ketone | A ketone in which the carbonyl group is attached to an aromatic ring. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| acetylcholinesterase | Homo sapiens (human) | Potency | 79.6407 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
| AR protein | Homo sapiens (human) | Potency | 0.0045 | 0.0002 | 21.2231 | 8,912.5098 | AID588515 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 30.6379 | 0.0006 | 57.9133 | 22,387.1992 | AID1259378 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 57.6658 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 22.2587 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531; AID588544 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 39.8107 | 0.3758 | 27.4851 | 61.6524 | AID588526 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 46.6131 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 30.6379 | 0.0002 | 29.3054 | 16,493.5996 | AID743080 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 7.3740 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895 |
| nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 34.6654 | 19.7391 | 45.9784 | 64.9432 | AID1159509 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 43.6412 | 0.0578 | 21.1097 | 61.2679 | AID1159528 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 68.5896 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 4 (5.06) | 18.7374 |
| 1990's | 17 (21.52) | 18.2507 |
| 2000's | 22 (27.85) | 29.6817 |
| 2010's | 30 (37.97) | 24.3611 |
| 2020's | 6 (7.59) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.
| This Compound (47.50) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (1.23%) | 5.53% |
| Reviews | 5 (6.17%) | 6.00% |
| Case Studies | 1 (1.23%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 74 (91.36%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||