General Information of Natural Product (ID: NP0563)
  Natural Product Name
1-Methyl-4-(Prop-1-En-2-Yl)Benzene
  Synonyms
1195-32-0; 1-Methyl-4-(prop-1-en-2-yl)benzene; 4-Isopropenyltoluene; Dehydro-p-cymene; 2-P-Tolylpropene; alpha,p-Dimethylstyrene; 1-Methyl-4-(1-methylethenyl)benzene; 4-Methylisopropenylbenzene; 2-(P-Methylphenyl)propene; p-cymenene; p,alpha-Dimethylstyrene; p-alpha-Dimethylstyrene; 1-Isopropenyl-4-methylbenzene; 1-Methyl-4-isopropenylbenzene; 1-methyl-4-prop-1-en-2-ylbenzene; p-alpha-Dimethyl styrene; Methyl-p-isopropenylbenzene; alpha-Methyl-P-methylstyrene; 4-Methyl-alpha-methylstyrene; BENZENE, 1-METHYL-4-(1-METHYLETHENYL)-; p-Mentha-1,3,5,8-tetraene; UNII-XC8HY3OB86; NSC 361058; Styrene, p,.alpha.-dimethyl-; p-Isopropenyl toluene; p,.alpha.-Dimethylstyrene; 1-methyl-4-prop-1-en-2-yl-benzene; XC8HY3OB86; ghl.PD_Mitscher_leg0.317; Methyl-4-(1-methylethenyl)-benzene; 1-Methyl-4-(1-methylethenyl)-benzene; Benzene, 1-methyl-4-(1-methylethenyl)-, homopolymer; Isopropenyltoluene, p-; Styrene, P-alpha-dimethyl-; 27599-43-5; FEMA No. 3144; EINECS 214-795-9; Dimethylstyrene, p-alpha-; p-Methyl-alpha-methylstyrene; cymenene; p-isopropenyltoluene; Cymenene (Related); NSC361058; Isopropenyl toluene c; P,alpha-Dimethylstyrol; alpha-p dimethylstyrene; 4,alpha-Dimethylstyrene; alpha,4-Dimethylstyrene; alpha-Dimethyl-p-styrene; p,alpha-Dimethyl-Styrene; p-alpha-Dimethyl-Styrene; .alpha.,p-Dimethylstyrene; p,a-Dimethylstyrene, 8CI; .alpha.,4-Dimethylstyrene; para-alpha-dimethyl styrene; Para- alpha-dimethylstyrene; 2-(4-Methylphenyl)propene; 1-p-Tolyl-1-methylethylene; 1-Methyl-4alpha-methylstyrene; para- .alpha.-Dimethylstyrene; p-Methyl-.alpha.-methylstyrene; 4-Methyl-.alpha.-methylstyrene; DTXSID7047564; 1-methyl-4.alpha.-methylstyrene; CHEBI:89920; FEMA 3144; 1-Isopropenyl-4-methylbenzene #; 4-CH3C6H4C(CH3)CH2; BAA19532; ZINC1584796; 3347AA; MFCD00036510; AKOS012525086; NSC-361058; 1-Methyl-4-(1-methylethenyl)benzene, 9CI; FT-0622103; I0693; p,alpha-Dimethylstyrene, >=98%, stabilized; F17145; A804307; Q27162104; alpha,4-Dimethylstyrene, stabilized with 4-t-butylcatechol
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  Formula C10H12
  Weight 132.2
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3
  InChI Key MMSLOZQEMPDGPI-UHFFFAOYSA-N
  Isomeric SMILES CC1=CC=C(C=C1)C(=C)C
  Canonical SMILES CC1=CC=C(C=C1)C(=C)C
  External Links PubChem ID 62385
CAS ID 1195-32-0

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia absinthium
  Factor Name: Chemotype Comparison [1]
              Species Info Factor Info
               Experiment Detail
Ten different plants of wormwood were collected in March 1997 from each one of the following four wild populations in the Spanish Pyrenees: Tallo de Aulet (prov. Huesca) and Pont de Suert, Sort and Farga de Moles (prov. Lleida). In three of the four populations studied, there was another chemotype, with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate. This chemotype, called chemotype B, was less frequent in the Pyrenees than the chemotype A, appearing only in 17% of the samples (two samples in TallO de Aulet and in Pont de Suert and three samples in Farga de Moles).
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               Factor Function
Two chemotypes were detected; a cis-epoxyocimene type (with more than 50% of this compound) which was predominant in all the populations, and a cis-epoxyocimene + chrysanthenyl acetate type (with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate). The distribution of these chemotypes had no relation with the altitude of the samples.
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               Factor Part Location NP Content
 
Chemotype (cis-epoxyocimene type)
Leaves Spain
NP Content: <0.03 %
 
Chemotype (cis-epoxyocimene + chrysanthenyl acetate type)
Leaves Spain
NP Content: <0.03 %
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [2]
              Species Info Factor Info
               Experiment Detail
Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996).
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               Factor Function
Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems).
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               Factor Part Location NP Content
 
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m
Aerial parts Patagonia, Argentina
NP Content: <0.1 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
Aerial parts Patagonia, Argentina
NP Content: 0.1 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: <0.1 %
      Species Name: Dittrichia graveolens
  Factor Name: Altitude Variation [3]
              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: 0.05 %
      Species Name: Fortunella japonica Lour. Swingle
  Factor Name: Heat Stress Treatment [4]
              Species Info Factor Info
               Experiment Detail
The investigation was carried out on kumquat [Fortunella japonica Lour. Swingle] cv. Ovale, grown in an experimental orchard located in central western Sardinia (Italy), receiving standard horticultural practices. Fruits were randomly harvested in March, when commercially mature (total soluble solids content/titratable acidity ratio = 5.24) and delivered to the laboratory immediately after harvest. Medium-size fruits free from defects were selected, placed into boxes (100 fruits per box), and grouped into two treatment groups of three boxes each (replications). The fruits of the first group were untreated (control fruit), whereas fruits of the second group were subjected to a standard treatment, water dipping at 50 &#8451 for 2 min, for extending the postharvest life of kumquat fruit. Dip treatment was performed as described previously. After treatments, fruits were allowed to dry at room temperature and stored for 21 days at 17 &#8451 and ca. 80% relative humidity (simulated shelf-life conditions). All analyses were performed following treatments and at the end of storage.
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               Factor Function
The concentration of the essential oil and the relative percentage of the individual components of the essential oil were not affected by HWD except for the minor compound p-menta-1,5-dien-1-ol, which increased after HWD.
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               Factor Part Location NP Content
 
Control: stored for 0 days
fruit Sardinia, Italy
NP Content: 0.18 %
 
HWD (Hot Water Dipping treatment: water dipping at 50 ℃ for 2 min) : stored for 0 days
fruit Sardinia, Italy
NP Content: 0.27 %
 
Control: stored for 21 days at 17 ℃
fruit Sardinia, Italy
NP Content: 0.36 %
 
HWD: stored for 21 days at 17 ℃
fruit Sardinia, Italy
NP Content: 0.31 %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [5]
              Species Info Factor Info
               Experiment Detail
Mentha rotundifolia leaves were collected in the second week of November 2004 in two localities of Algeria (Rouina: altitude 250 m, Miliana: altitude 780 m) within the region of Ain-Defla located in northern Algeria.
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               Factor Function
Thirty-nine compounds were identified in leaf oil of sample 1 (Rouina, Algeria), the main one being cis-piperitone oxide. Thirty-nine compounds were identified in leaf oil of sample 2 (Miliana, Algeria). The main one being piperitenone oxide.
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               Factor Part Location NP Content
 
Locality: Miliana, Algeria; Altitude 780 m
Leaves Algeria
NP Content: 0.4 %
      Species Name: Thymus leucostomus
  Factor Name: Altitude Variation [6]
              Species Info Factor Info
               Experiment Detail
Herbal parts were collected from A = Eskisehir: Suluagac village in Turkey, altitude 1100 m, in July 1990 and B = Corum: Osmancik, Berk village in Turkey, altitude 580-600 m, on 22 June 1993.
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               Factor Function
One chemotype (Suluagac village, Eskisehir, Turkey) contained carvacrol (21.59%), p-cymene (17.80%) and thymol (14.10%); and the other chemotype (Berk village, Corum, Turkey) contained alpha-terpinyl acetate (23.80%), borneol (12.85%), linalool (13.67%) and thymol (11.31%) as major constituents.
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               Factor Part Location NP Content
 
Locality: Suluagac village, Eskisehir, Turkey; Altitude 1100 m
Herbal parts Turkey
NP Content: 0.07 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [7]
              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 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.2 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [9]
              Species Info Factor Info
               Experiment Detail
3-year old single shoot V. vinifera plants (cultivar Pinot noir 18 Gm grafted on Kober 5BB, 51 plants) potted in 3L pots in a sandy loam soil were used. All plants were well watered (200 mL per day) at the beginning of the experiment (04.06.2010; DAY 0; 5 plants) and water was supplied to all control plants once every day (250 mL per day), whereas water supply of stressed plants was stopped. Physiological measurements and sampling of leaves took place on 07.06.2010 (DAY 3; 5 control, 5 stressed plants), 10.06.2010 (DAY 6; 5 control, 5 stressed plants) and 12.06.2010 (DAY 8; 5 control, 10 stressed plants). Due to very hot weather conditions in June 2010 the experiment was stopped after 8 days and 12 available control plants were used to restart the drought treatment with 6 control and 6 stressed plants on 11.06.2010 and all plants were measured on 15.06.2010 (DAY 5). The mean leaf temperatures at midday were: 25 ℃ (04.06.2010; DAY 0), 31.9 ℃ (07.06.2010; DAY 3), 30.8 ℃ (15.06.2010; DAY 5), 35.8 ℃ (10.06.2010; DAY 6) and 35.7 ℃ (12.06.2010; DAY 8). The mean PAR radiation per day (measured from 6:00 am till 7:00 pm) was 144.1 µmol m-2 s-1. Each plant was used only once for physiological measurements and sampling of leaves.On every day of the experiment (day 0, 3, 5, 6, 8) the pot weight and the volumetric soil moisture content (ThetaProbe ML2x and handheld data logger Moisture Meter HH2, Delta-T Devices, Cambridge, United Kingdom) was recorded. The water potential (PWSC Model 3000, Soilmoisture Equipment Corporation, Santa Barbara, USA) was determined for the 6th leaf (representing the insertion level of the shoot from the basis) of every plant and measurement day. Chlorophyll fluorescence and gas exchange parameters of light adapted leaves were determined with the 4th and 5th leaf, whereas dark adaptation was performed only with the 5th leaf. Immediately after these non-invasive measurements, the 5th leaf was harvested, frozen in liquid nitrogen and further used for the measurement of polyphenols, selected primary metabolites and volatiles (VOCs).
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               Factor Function
The content of different groups of primary and secondary metabolites is significantly influenced by severe drought stress in grapevine leaves. The content of the majority of the metabolites (around 60% of primary metabolites, around 85% of polyphenols and about 40% of the detected and identified VOCs) increased upon drought stress treatment. Among these especially the primary metabolites citric acid and glyceric acid were strongly influenced by the short as well as the prolonged drought stress treatment, whereas all polyphenols were only induced upon the prolonged drought stress treatment.
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               Factor Part Location NP Content
 
Normal condition
Leaves Vienna, Austria
NP Content: 838.9 ± 444.3 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 1176.8 ± 637.8 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 901.3 ± 246.4 peak areas
References
1 Essential Oil of Artemisia absinthium L. from the Spanish Pyrenees
2 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
3 Chemical Profle of the Dittrichia graveolens (Desf.) Greuter Essential Oil of Lebanese Origin
4 Influence of postharvest hot water treatment on nutritional and functional properties of kumquat (Fortunella japonica Lour. Swingle Cv. Ovale) fruit
5 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
6 Essential Oil of Thymus leucostomus Hausskn. et Velen. var. leucostomus
7 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey
8 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey
9 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)