Details of Natural Product (NP)

General Information of Natural Product (ID: NP0157)
  Natural Product Name
Methyl Cinnamate
  Synonyms
Methyl cinnamate; 103-26-4; Methyl trans-cinnamate; 1754-62-7; Methyl (E)-cinnamate; Cinnamic acid methyl ester; Methyl (E)-3-phenylprop-2-enoate; Methyl cinnamylate; Methyl 3-phenylacrylate; methyl-3-phenylprop-2-enoate; trans-Methyl cinnamate; (E)-Methyl cinnamate; Methyl 3-phenyl-2-propenoate; trans-Cinnamic acid methyl ester; Methyl 3-phenylpropenoate; Methylcinnamate; UNII-533CV2ZCQL; Methyl trans-3-phenyl-2-propenoate; methyl (2E)-3-phenylprop-2-enoate; Cinnamic acid, methyl ester, (E)-; 533CV2ZCQL; 2-PROPENOIC ACID, 3-PHENYL-, METHYL ESTER, (E)-; CHEBI:6857; Methyl (2E)-3-phenylacrylate; CINNAMIC ACID, METHYL ESTER; Methyl (E)-3-phenyl-2-propenoate; trans-Methyl 3-Phenyl-2-propenoate; 2-propenoic acid, 3-phenyl-, methyl ester, (2E)-; MFCD00008458; (E)-3-Phenylacrylic acid methyl ester; NSC 9411; SemaSORB 9815; Methyl cinnamate (natural); Methyl cinnamate, (E); FEMA No. 2698; EINECS 203-093-8; AI3-00579; cis-methyl cinnamate; Cinnamic acid methyl; methyl trans cinnamate; methyl-trans-cinnamate; Nat. Methyl Cinnamate; EC 203-093-8; DSSTox_CID_22151; DSSTox_RID_80147; DSSTox_GSID_44314; WLN: 1OV1U1R; ghl.PD_Mitscher_leg0.369; methyl-3 phenylprop-2-enoate; CHEMBL55060; Methyl trans-3-Phenylacrylate; Methyl trans-cinnamate, 99%; SCHEMBL101530; Methyl (E)-3-phenylpropenoate; Benzeneacrylic acid methyl ester; DTXSID5044314; Methyl (2E)-3-phenylpropenoate; NSC9411; 3-Phenyl-2-propenoic acid methyl; ZINC896129; NSC-9411; Tox21_301384; s6221; STL582416; Methyl cinnamate, >=99.0% (GC); AKOS015890136; CS-W017928; HY-W017212; Methyl (2E)-3-phenyl-2-propenoate #; trans-3-Phenylacrylic Acid Methyl Ester; NCGC00255910-01; DS-17838; LS-13765; CAS-1754-62-7; Methyl trans-cinnamate, analytical standard; Methyl trans-cinnamate, >=98%, FCC, FG; (E)-3-Phenyl-2-propenoic acid methyl ester; (E)-methyl ester 3-phenyl-2-propenoic acid; (2E)-3-Phenyl-2-propenoic acid methyl ester; trans-3-Phenyl-2-propenoic acid methyl ester; C06358; Methyl cinnamate, analytical reference material; Methyl cinnamate, natural, >=98%, FCC, FG; P16737; trans-3-phenyl-prop-2-enoic acid methyl ester; Q204178; J-000917; J-011115; J-522598; Q-100258
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  Formula C10H10O2
  Weight 162.18
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
  InChI Key CCRCUPLGCSFEDV-BQYQJAHWSA-N
  Isomeric SMILES COC(=O)/C=C/C1=CC=CC=C1
  Canonical SMILES COC(=O)C=CC1=CC=CC=C1
  External Links PubChem ID 637520
CAS ID 103-26-4
NPASS ID NPC3672
CHEMBL ID CHEMBL55060
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia ferganensis
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
The leaves of aerial parts were collected in Heshuo county of Xinjiang province in China in July 2003 (a vegetative stage), June 2003 (a budding stage); and August 2003 (a flowering stage), respectively.
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               Factor Function
Only 23 constituents were present at the budding stage, while 24 and 26 at the flowering and vegetative stages, respectively. p-Cymene and gamma-terpinene were not detected at the vegetative stage of the plant. During the budding stage, butyric, beta-caryophyllene, geranyl acetate and cis-jasmone could not be detected. Benzaldehyde was observed only at the vegetative stage. Variations were also observed in quantity. In all cases the analyzed oils were characterized by the high concentration of alpha-thujone, ranging in amount from 37.0% at the vegetative stage to 54.8% at the budding stage. The concentration of alpha-thujone at the flowering stage (49.0%) was lower than the budding stage, but higher than the vegetative stage. The concentration of cis-chrysanthenyl acetate varied between 23.5% and 7.2%, respectively, at the vegetative and budding stages. At the vegetative stage the concentration of 1,8-cineole was observed to be the lowest. It was highest at the budding stage, representing 10.4%, then decreased gradually to 8.8% at the flowering stage. The concentration of beta-thujone was relatively low at the vegetative stage, representing 8.6%, and then increased to 10.5% at the budding stage. When flowers appeared it was found to vary a little. Finally, the concentration of sabinyl acetate ranged from 10.2% (vegetative stage) to 6.5% (flowering stage).
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               Factor Part Location NP Content
 
Vegetative stage
 Leaves Heshuo, Xinjiang, China
NP Content: 0.7 %
 
Budding stage
 Leaves Heshuo, Xinjiang, China
NP Content: 0.4 %
 
Aerial part: Flowering stage
 Leaves Heshuo, Xinjiang, China
NP Content: 0.4 %
      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: 1.9 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
 Aerial parts Patagonia, Argentina
NP Content: <0.1 %
      Species Name: Lychnophora pinaster
  Factor Name: Seasonal Variation [3]
              Species Info Factor Info
               Experiment Detail
Plants from Horto de Plantas Medicinais of Universidade Federal de Lavras (UFLA) were cultivated in the form of a randomized block with six replications in an experimental field at Setor de Horticultura, UFLA, in Lavras city (S 21° 14′, W 44° 59′, 920 m). Samples were collected four times at 3-month intervals from March to December 2004.
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               Factor Function
There was a significant difference for oil contents in the different seasons. The lowest oil content was obtained in the summer (about 50% inferior to the other seasons). Methyl (E)-cinnamate was obtained as the major compound (86-90%) of the 14 identified components.
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               Factor Part Location NP Content
 
Harvesting time: Spring
 Aerial parts Brazil
NP Content: 86.3 %
 
Harvesting time: Summer
 Aerial parts Brazil
NP Content: 93 %
 
Harvesting time: Autumn
 Aerial parts Brazil
NP Content: 92.2 %
 
Harvesting time: Winter
 Aerial parts Brazil
NP Content: 90.5 %
      Species Name: Ocimum basilicum
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
Aerial parts of Ocimum basilicum var. purpurascens Benth, Ocimum basilicum var. dianatnejadii Salimi at flowering stage were collected from plants grown in Experimental Station of Pykan Shahr, near Tehran. Elevation 1215 m above sea level, latitude 35° 42′ North, 51° 8′ East, average humidity 36% and climatic category semi-arid.
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               Factor Function
Methyl chavicol (43.0%) and linalool (28.9%) were identified as the major compounds in the oil of O. basilicum var. purpurascens, while methyl chavicol (37.6%), linalool (33.4%) and alpha-cadinol (5.7%) were the major constituents in the oil of O. basilicum var. dianatnejadii.
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               Factor Part Location NP Content
 
Ocimum basilicum var. purpurascens Benth
 Aerial parts Iran
NP Content: 0.2 %
      Species Name: Ocimum basilicum L
  Factor Name: Chemotype Comparison [5]
              Species Info Factor Info
               Experiment Detail
The study was conducted in North-Central Anatolia under semi arid conditions. Seeds of 18 basil landraces (O. basilicum L.) were collected from local farms and home gardens in Turkey. To examine essential oil composition of the basil landraces without environmental influences, the plants were grown under identical (same environmental and soil conditions) conditions. Seeds were sown on a medium (1:1:1 washed sand, horse manure and field soil) in greenhouse conditions on March 25, 2003. Seedlings were grown until the 3-5 leaf stage. The seedlings were transplanted into pilots in the Gaziosmanpasxa University Experimental Research Station on May 15, 2003. The plants were harvested at the full blooming stage and dried at 35 ℃ for essential oil isolation.
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               Factor Function
Variation of essential oils in the landraces was subjected to cluster analysis, and seven different chemotypes were identified. They were (1) linalool, (2) methyl cinnamate, (3) methyl cinnamate/linalool, (4) methyl eugenol, (5) citral, (6) methyl chavicol (estragol), and (7) methyl chavicol/citral. Methyl chavicol with high citral contents (methyl chavicol/citral) can be considered as a 'new chemotype' in the Turkish basils.
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               Factor Part Location NP Content
 
Chemotype (methyl (E)-cinnamate-rich type)
 Leaves Turkey
NP Content: 61 %
 
Chemotype (methyl (E)-cinnamate-rich and linalool-rich type)
 Leaves Turkey
NP Content: 30.3 %
 
Chemotype (methyl eugenol-rich type)
 Leaves Turkey
NP Content: 4.6 %
 
Chemotype (methyl chavicol-rich type)
 Leaves Turkey
NP Content: 0.4 %
 
Chemotype (methyl chavicol and citral-rich type)
 Leaves Turkey
NP Content: 0.7 %
References
1 Seasonal Analyses of the Essential Oil of Artemisia ferganensis
2 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
3 Seasonal Variation in Essential Oils of Lychnophora pinaster Mart.
4 Essential oil composition of four Ocimum species and varieties growing in Iran
5 Variability in essential oil composition of Turkish basils (Ocimum basilicum L.)