Details of Natural Product (NP)

General Information of Natural Product (ID: NP0569)
  Natural Product Name
Benzyl Benzoate
  Synonyms
BENZYL BENZOATE; 120-51-4; Ascabiol; Benzoic acid, phenylmethyl ester; Benylate; Novoscabin; Benzoic acid benzyl ester; Benzoic acid, benzyl ester; Scabitox; Scabiozon; Ascabin; Scobenol; Benzyl phenylformate; Phenylmethyl benzoate; Benzylets; Colebenz; Peruscabin; Scabagen; Scabanca; Vanzoate; Scabide; benzylbenzoate; Benzyl benzenecarboxylate; Venzonate; Benzylis benzoas; Benzyl alcohol benzoic ester; Benzylester kyseliny benzoove; BENZOIC ACID PHENYLMETHYLESTER; FEMA No. 2138; NSC 8081; UNII-N863NB338G; CHEMBL1239; Antiscabiosum; CHEBI:41237; N863NB338G; NSC-8081; MFCD00003075; NCGC00094981-03; Peruscabina; DSSTox_CID_9153; Benzylum benzoicum; DSSTox_RID_78686; DSSTox_GSID_29153; Benzoesaeurebenzylester; Caswell No. 082; Benzylbenzenecarboxylate; Venzoate; FEMA Number 2138; Benzyl benzoate, analytical standard; Benzyl benzoate (natural); BZM; CAS-120-51-4; SMR000471875; HSDB 208; EINECS 204-402-9; Benzylester kyseliny benzoove [Czech]; EPA Pesticide Chemical Code 009501; benzylbenzoat; BRN 2049280; Benzyl benzoate [USP:JAN]; Acarobenzyl; Benzevan; Bengal; benzyl-benzoate; Benzoic acid phenylmethyl ester; AI3-00523; 1dzm; Benylate (TN); benzoic acid benzyl; Spectrum_001240; Benzoic acid-benzyl ester; Spectrum2_000532; Spectrum3_001757; Spectrum4_000773; Spectrum5_001128; WLN: RVO1R; Benzyl benzoate, >=99%; EC 204-402-9; SCHEMBL3038; BENZYL BENZOATE BP98; BSPBio_003494; KBioGR_001186; KBioSS_001720; 4-09-00-00307 (Beilstein Handbook Reference); MLS001066412; MLS001336003; MLS001336004; DivK1c_000204; SPECTRUM1503002; SPBio_000543; Benzyl benzoate (JP17/USP); ZINC1021; DTXSID8029153; BENZOIC ACID,BENZYL ESTER; HMS500K06; KBio1_000204; KBio2_001720; KBio2_004288; KBio2_006856; KBio3_002714; NSC8081; NINDS_000204; HMS1921P16; HMS2092F20; HMS2269D24; Pharmakon1600-01503002; HY-B0935; Tox21_111372; Tox21_201337; Tox21_303418; BDBM50134035; CCG-39578; NSC758204; s4599; STL183088; AKOS003495939; Benzyl benzoate, >=99%, FCC, FG; Tox21_111372_1; DB00676; MCULE-4369643785; NSC-758204; IDI1_000204; Benzyl benzoate, for synthesis, 99.0%; NCGC00094981-01; NCGC00094981-02; NCGC00094981-04; NCGC00094981-05; NCGC00094981-07; NCGC00257502-01; NCGC00258889-01; AC-17033; LS-14279; SBI-0051748.P002; DB-041563; B0064; FT-0622708; Benzyl benzoate, natural, >=99%, FCC, FG; Benzyl benzoate, ReagentPlus(R), >=99.0%; Benzyl benzoate, SAJ first grade, >=98.0%; Benzyl benzoate, tested according to Ph.Eur.; A14577; A19449; Benzyl benzoate, SAJ special grade, >=99.0%; D01138; AB00052298_07; Benzyl benzoate, Vetec(TM) reagent grade, 98%; Benzyl benzoate, meets USP testing specifications; Q413755; SR-01000763773; Benzoic acid-benzyl ester 5000 microg/mL in Hexane; Q-200696; SR-01000763773-2; BRD-K52072429-001-06-1; Benzoic acid benzyl ester; Benzoic acid phenylmethyl ester; Benzyl benzoate, certified reference material, TraceCERT(R); Benzyl benzoate, United States Pharmacopeia (USP) Reference Standard; Benzyl benzoate, Pharmaceutical Secondary Standard; Certified Reference Material
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  Formula C14H12O2
  Weight 212.24
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2
  InChI Key SESFRYSPDFLNCH-UHFFFAOYSA-N
  Isomeric SMILES C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2
  Canonical SMILES C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2
  External Links PubChem ID 2345
CAS ID 120-51-4
NPASS ID NPC118343
CHEMBL ID CHEMBL1239
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [1]
              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
 
Leaf: Fragaria vesca cv. Baron von Solemacher
 Leaves Poland
NP Content: <0.05 %
 
Leaf: Fragaria vesca cv. Rugia
 Leaves Poland
NP Content: <0.05 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
The branches of pine were collected in July, 1996 in 15 different locations in Lithuania in the following regions: Western part (Silute, Jurbarkas, Kursiu Nerija), Eastern part (Salcininkai, Zarasai, Moletai), Southern part (Varena, Trakai, Radviliskis) and central part (Ukmerge, Jonava, Kaisiadorys). The branches in each location were collected from the trees in approximately 1 km radius.
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               Factor Function
More than 70 constituents were identified (64 positively and 10 tentatively) in the oils. alpha-Pinene (18.5-33.0%) and delta-3-carene (9.1-24.6%) were dominating constituents with the only one exception when the germacrene-4-ol content in one of the samples was 13.2%. The important bornyl acetate content varied from 0.5% to 3.0%. The main sesquiterpenes were beta-caryophyllene, germacrene D, bicyclogermacrene, delta-cadinene, gamma-cadinene, germacrene D-4-ol, cubenol (2.0-5.1%) and alpha-cadinol (1.9-7.7%).
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               Factor Part Location NP Content
 
Locality: Jonava, Lithuania
 Branches Jonava, Lithuania
NP Content: 0.2 %
 
Locality: Jurbarkas, Lithuania
 Branches Jurbarkas, Lithuania
NP Content: 0.1 %
 
Locality: Kaisiadorys, Lithuania
 Branches Kaisiadorys, Lithuania
NP Content: 0.1 %
 
Locality: Moletai, Lithuania
 Branches Moletai, Lithuania
NP Content: 0.1 %
 
Locality: Neringa (Smiltyne), Lithuania
 Branches Neringa (Smiltyne), Lithuania
NP Content: 0.1 %
 
Locality: Radviliskis, Lithuania
 Branches Radviliskis, Lithuania
NP Content: 0.1 %
 
Locality: Salacininkai, Lithuania
 Branches Salacininkai, Lithuania
NP Content: 0.1 %
 
Locality: Silute, Lithuania
 Branches Silute, Lithuania
NP Content: 0.1 %
 
Locality: Trakai, Lithuania
 Branches Trakai, Lithuania
NP Content: 0.1 %
 
Locality: Ukmerge, Lithuania
 Branches Ukmerge, Lithuania
NP Content: 0.05 %
 
Locality: Varena, Lithuania
 Branches Varena, Lithuania
NP Content: 0.1 %
 
Locality: Vilnius, Lithuania
 Branches Vilnius, Lithuania
NP Content: 0.1 %
 
Locality: Zarasai (Sunele), Lithuania
 Branches Zarasai (Sunele), Lithuania
NP Content: 0.1 %
      Species Name: Solidago virgaurea
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of Solidago virgaurea plants were randomly collected from the wild at two different altitudes, as described below, during the 2000 vegetation period. All the collections of the plant samples were carried out during massive bud formation and the beginning of flowering stage. Sample # 1, LTS00-46; 10 kg of the sample was collected on July 31, 2000 at LAT: 51° 07′ LON: 81° 10′ HEI 290 m from Altai land, Lokteev district, near the village of NovoMikhaylovskoe, on the left bank of the Aley River, outskirts of pine forest, fire area, sandy soils. Sample # 2, LTS00-57; 5.6 kg of the sample was collected on August 3, 2000 at LAT 51° 14′ LON 82° 28′ HEI 650 m from Altai land, Kur'in district, around the Kolyvanm quarries, with diverse turf grasses, along the river bank of Aley.
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               Factor Function
The main components from 290 m were alpha-pinene (36.5%), myrcene (14.8%), beta-caryophyllene (10.5%), germacrene D (8.2%), beta-pinene (7.1%) and limonene+beta-phellandrene (6.4%). The oil from the sample collected at 650 m had benzyl benzoate (57.0%), beta-caryophyllene (6.3%), germacrene D (6.0%), alpha-pinene (4.4%) and alpha-humulene (4.0%) as major components, suggesting polymorphism or the existence of different chemoytpes.
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               Factor Part Location NP Content
 
Locality: Lokteev district, Russia; Altitude 290 m
 Flowers Russia
NP Content: 0.3 %
 
Locality: Kur'in district, Russia; Altitude 650 m
 Flowers Russia
NP Content: 57 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [4]
              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: <0.05 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [5]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. flavum were collected in different periods from December to July 2006, from plants growing along the Ionic coast of Sicily (Italy). LF 1-LF 2-LF 3: represent the composition of leaf oils of plant samples collected in December (vegetative stage), February (pre-flowering stage) and April (budding stage) respectively; FL: flower oil; FR: fruit oil.
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               Factor Function
Some components, in all investigated plant parts, remained more or less constant during all the different phases of the plant cycle life. Worthy of note, considering the leaf oils, was that beta-pinene, limonene and germacrene D increased in the pre-flowering stage, while a series of esters and alpha-copaene, beta-caryophyllene, viridiflorol, Tmuurolol and phytol increased in the budding stage (LF3); the vegetative stage oil is generally characterized by a rich chemical composition and some constituents such as isoamyl hexanoate, alpha-humulene, bicyclogermacrene, beta-bisabolene and alpha-bisabolol reached their highest levels in this oil. In the flower oil, linalool and 1-octen-3-yl acetate were the main components compared to the amounts found in the other oils. Fruit oil composition was relatively oil poor, with beta-bisabolene, caryophyllene oxide, cadin-4-en-1-ol and phytone as the major constituents.
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               Factor Part Location NP Content
 
Harvesting time: April; budding stage
 Leaves Italy
NP Content: 0.3 %
 
Flower oil
 Flowers Italy
NP Content: 0.1 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [6]
              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: 1300.8 ± 589.9 peak areas
 
Dry 3-5 days
 Leaves Vienna, Austria
NP Content: 1407.5 ± 988.1 peak areas
 
Dry 6-8 days
 Leaves Vienna, Austria
NP Content: 1045.1 ± 827.9 peak areas
References
1 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
2 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
3 Volatile Oil-Bearing Flora of Siberia VIII: Essential Oil Composition and Antimicrobial Activity of Wild Solidago virgaurea L. from the Russian Altai
4 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
5 Seasonal Variations of Teucrium flavum L. Essential Oil
6 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)