Details of Natural Product (NP)

General Information of Natural Product (ID: NP0294)
  Natural Product Name
Damascenone
  Synonyms
Damascenone; beta-Damascenone; 23696-85-7; 23726-93-4; trans-beta-Damascenone; 1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one; 2-BUTEN-1-ONE, 1-(2,6,6-TRIMETHYL-1,3-CYCLOHEXADIEN-1-YL)-; (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one; trans-damascenone; UNII-U66V25TBO0; .beta.-Damascenone; (E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; U66V25TBO0; (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (2E)-; 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)-; 2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadiene; 1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2E-buten-1-one; Damascenone (natural); fermentone; FEMA No. 3420; EINECS 245-833-2; EINECS 245-844-2; Damascenone, trans-; damascenone (e-beta); (E)-beta-damascenone; beta-(E)-damascenone; trans-.beta.-Damascenone; (E)-.beta.-Damascenone; .beta.-(E)-Damascenone; DSSTox_CID_21397; DSSTox_GSID_41397; SCHEMBL80947; DISCONTINUED, UNSTABLE'; Damascenone, analytical standard; CHEMBL3733030; CHEBI:67251; 4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-4-one; DTXSID90885242; HY-N2543; Tox21_304001; 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E); LMPR01070304; MFCD00101024; s6431; AKOS015914961; ZINC100070359; NCGC00357220-01; AC-34815; BS-16271; CAS-23696-85-7; CS-0022815; 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene; 2,6,6-trimethyl-1-crotonoyl-1,3-cyclohexadiene; A816852; Q416126; (E)-beta-Damascenone 1000 microg/mL in Acetonitrile; Damascenone, certified reference material, TraceCERT(R); 4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl)but-2-en-4-one; (E)-1-(2,6,6-trimethylcyclohexa-1,3-dienyl)but-2-en-1-one; (2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one; Damascenone, natural, 1.1-1.3 wt. % (190 proof ethanol), FG; (2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one; 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, trans-
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  Formula C13H18O
  Weight 190.28
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
  InChI Key POIARNZEYGURDG-FNORWQNLSA-N
  Isomeric SMILES C/C=C/C(=O)C1=C(C=CCC1(C)C)C
  Canonical SMILES CC=CC(=O)C1=C(C=CCC1(C)C)C
  External Links PubChem ID 5366074
CAS ID 23696-85-7
NPASS ID NPC37644
CHEMBL ID CHEMBL3733030
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Dittrichia graveolens
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
Wild growing D. graveolens samples were collected from Bekaa-877′ (4 samples) and Sannine-1842′ (3 samples) during the flowering period, between September and November of 2003.
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               Factor Function
The major differences in oil composition between the two populations are the variation in the concentrations of T-cadinol and borneol. The differences can also be ascribed to the distinct climatic pattern of the two samples: Sannine is located in the Mount Lebanon chain of mountains and characterized by heavy precipitations and snow, while the Bekaa valley is shielded by this same chain of mountains, resulting in dry summers and cold winters with less humidity and precipitations.
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               Factor Part Location NP Content
 
Locality: Bekka, Lebanon; Altitude 877 m
 Leaves and flowers Lebanon
NP Content: 0.01 %
 
Locality: Sannine, Lebanon; Altitude 1842 m
 Leaves and flowers Lebanon
NP Content: 0.06 %
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [2]
              Species Info Factor Info
               Experiment Detail
Whole leaves and inflorescences of two wild strawberry cultivars ('Rugia' and 'Baron von Solemacher') harvested in 2008 during the agrotechnical experiment performed by Department of Vegetable and Medicinal Plants, University of Life Sciences in Lublin, were used as a material for determinations. Samples were collected before noon at sunny and dry days at the beginning of wild strawberry's flowering stage. Material was dried up to 35 ℃ in shadow and air just after the harvest.
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               Factor Function
Depending on a cultivar, air-dry inflorescences from wild strawberry contain from 0.21% ('Baron von Solemacher' cv.) to 0.30% ('Rugia' cv.), whereas leaves contains from 0.46% ('Baron von Solemacher' cv.) to 0.62% ('Rugia' cv.) of essential oils. GC/MS analysis of essential oils achieved from studied materials revealed presence of 70 (including 59 identified) compounds in leaves of 'Rugia' cv. and 58 (including 50 identified) compounds in leaves of 'Baron von Solemacher' cv. Essential oils from inflorescences of 'Rugia' cv. contained 52 (including 47 identified), while 'Baron von Solemacher' cv. contained 54 (including 46 identified) compounds. The chromatographic analyses by GC-MS revealed that myrthenol, nonal, linalool and phthalide dibuthyl dominated in essential oils obtained from leaves, while myrthenol, citronelol, linalool and geraniol - from those of inflorescences. There were qualitative differences between oil components at both studied materials and differentiation between both cultivars, as well.
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               Factor Part Location NP Content
 
Inflorescence: Fragaria vesca cv. Baron von Solemacher
 Inflorescence Poland
NP Content: <0.05 %
 
Inflorescence: Fragaria vesca cv. Rugia
 Inflorescence Poland
NP Content: <0.05 %
 
Leaf: Fragaria vesca cv. Rugia
 Leaves Poland
NP Content: 0.66 %
      Species Name: Pulicaria dysenterica
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of P. dysenterica were collected during the flowering stage from two different locations in Greece in August 2002. Sample A: Katara (Perfecture Trikala). Sample B: Arahova (Perfecture Viotia).
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               Factor Function
Fifty-four components were identified representing 80.5% (sample A) and 72.6% (sample B) of the total oils. The main components in sample A were (Z)-nerolidol (11.2%), caryophyllene oxide (9.1%) and (E)-nerolidol (6.6%), while those of sample B were beta-caryophyllene (12.8%), caryophyllene oxide (12.8%) and (E)-nerolidol (6.9%).
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               Factor Part Location NP Content
 
Locality: Katara, Perfecture Trikala, Greece
 Aerial parts Greece
NP Content: <0.1 %
 
Locality: Arahova, Perfecture Viotia, Greece
 Aerial parts Greece
NP Content: <0.1 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
 Flowering aerial parts Turkey
NP Content: 0.1 %
 
Salvia euphratica var. leiocalycina
 Flowering aerial parts Turkey
NP Content: 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
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               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
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               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
 Aerial parts Iran
NP Content: 0.1 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected during the flowering period in July 2002 from the Dumluca Mountain in the vicinity of Divrigi village of Sivas city at 1900 m altitude and Saksagan Gorge in Saimbeyli village of Adana city at 1900 m altitude.
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               Factor Function
The flower, stem and root oils of T. cadmeum ssp. orientale collected from the Adana location were characterized with alpha-thujone (25%, 5.2%), cis-linalool oxide (6.8%, 12.8%), trans-chrysanthenyl acetate (5.8%, 8.5%) for flower and stem oils, and beta-eudesmol (10.3%, 6.2%, 13.8%); in addition, stem oil contained 1,8-cineole (6.6%) and root oil contained hexadecanoic acid (6.0%), spathulenol (5.8%) and beta-muurolol (5.3%). The flower and stem oils of T. cadmeum ssp. orientale collected from the Sivas location were characterized with camphor (25.9%, 14.8%), borneol (15.4%, 25.8%) and alpha-thujone (7.8%, 5.5%); in addition, stem oil contained 1,8-cineole (7.4%) and root oil contained nonacosane (16.2%), spathulenol (6.8%) and hexadecanoic acid (5.8%).
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               Factor Part Location NP Content
 
Stem: (Locality: Adana, Turkey)
 Stems Adana, Turkey
NP Content: <0.1 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [7]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. chamaedrys were collected at the flowering stage in June 2004 near Corti, Corsica, France and near Oristano, Sardinia, Italy
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               Factor Function
The Corsican and Sardinian oils of T. chamaedrys investigated in this study were qualitatively similar but they differed by the amount of their major components. The major components were beta-caryophyllene (29.0% and 27.4%, respectively) and germacrene D (19.4% and 13.5%, respectively), followed by alpha-humulene (6.8%) and delta-cadinene (5.4%) in the Corsican oil and by caryophyllene oxide (12.3%) and alpha-humulene (6.5%) in the Sardinian oil. These quantitative differences are also noticeable on the amounts of the different class compounds. Especially, the monoterpene hydrocarbons amounted for 10.3% and 4.1% in Sardinian and Corsican oils respectively and the oxygenated sesquiterpenes amounted for 18.9% and only 7.4% in both oils, respectively. Both oils were qualitatively rather similar in comparison with those reported in the literature from various geographic regions. However, among the 87 components identified in this study, 47 minor components (< 0.6%) reported were identified for the first time in T. chamaedrys oil. This study confirms the quantitative variability of the major components according to the plant origin.
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               Factor Part Location NP Content
 
Locality: Corti, Corsica, France
 Aerial parts France
NP Content: 0.1 %
 
Locality: Oristano, Sardinia, Italy
 Aerial parts Italy
NP Content: 0.1 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
 Aerial parts Eskisehir, Turkey
NP Content: <0.1 %
References
1 Chemical Profle of the Dittrichia graveolens (Desf.) Greuter Essential Oil of Lebanese Origin
2 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
3 Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece
4 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
5 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
6 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
7 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
8 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey