Details of Natural Product (NP)

General Information of Natural Product (ID: NP0387)
  Natural Product Name
Menthofuran
  Synonyms
Menthofuran; 494-90-6; Menthofurane; 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran; BENZOFURAN, 4,5,6,7-TETRAHYDRO-3,6-DIMETHYL-; 3,9-Epoxy-p-mentha-3,8-diene; 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran; p-Mentha-3,8-diene, 3,9-epoxy-; 4,5,6,7-Tetrahydro-3,6-dimethylcoumarone; CHEBI:50542; 17957-94-7; FEMA No. 3235; EINECS 207-795-5; NSC 315249; MFCD00041851; (+/-)-menthofuran; 3,8-diene; (R)-4,5,6,7-tetrahydro-3,6-dimethylbenzofuran; (S)-3,6-Dimethyl-4,5,6,7-tetrahydrobenzofuran; (R)-(+)-Menthofuran; 3,6-dimethyl-4,5,6,7-tetrahydrobenzofuran; DSSTox_CID_5534; DSSTox_RID_77820; DSSTox_GSID_25534; p-Mentha-3, 3,9-epoxy-; SCHEMBL1472618; CHEMBL1522900; DTXSID9025534; ALBB-025049; Tox21_200722; BDBM50418084; NSC315249; AKOS015906818; MCULE-5659713573; NSC-315249; SB47674; 3,9-Epoxy-(+)-p-Mentha-3,8-diene; NCGC00090822-01; NCGC00090822-02; NCGC00258276-01; AS-76978; CAS-494-90-6; DB-065282; Benzofuran,5,6,7-tetrahydro-3,6-dimethyl-; FT-0617128; FT-0772068; p-Mentha-3,8-diene, 3,9-epoxy- (8CI); 3,6-dimethyl-4,5,6,7-tetrahydro-benzofuran; C09868; 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran #; 4,5,6,7-Tetrahydro-3,6-dimethyl-(R)-Benzofuran; Q6817554; 4,5,6,7-TETRAHYDRO-3,6-DIMETHYL-BENZOFURAN; 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, >=95%
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  Formula C10H14O
  Weight 150.22
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3
  InChI Key YGWKXXYGDYYFJU-UHFFFAOYSA-N
  Isomeric SMILES CC1CCC2=C(C1)OC=C2C
  Canonical SMILES CC1CCC2=C(C1)OC=C2C
  External Links PubChem ID 329983
CAS ID 494-90-6
NPASS ID NPC59035
CHEMBL ID CHEMBL1522900
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Mentha piperita
  Factor Name: Drought Stress Treatment; NaCl Treatment [1]
              Species Info Factor Info
               Experiment Detail
Peppermint plants were initiated from rhizome cuttings (10 cm long) supplied by Jahad Daneshgahi in March 2009. According to the method described by Farahani et al., (2009), seventy five peppermint samples were notified above were transferred into pots (25 cm head diameter × 20 cm height) filled with sandy loam soil (soil average amount of 5580 gr in each pot). This experiment was carried out using a randomized compllete block design with 3 replications. The factors studied included 5 levels of water deficit stress that were D1 (100% field capacity), D2 (85% field capacity), D3 (70% field capacity), D4 (60% field capacity) and D5 (45% field capacity), respectively. In order to determine the soil moisture rate of 100% field capacity, 24 h after irrigation we selected 5 field soil samples by sampling drill, then samples were weighed by electrical scale and placed under 105 ℃ in electrical oven for 48 h. Field soil samples were selected for determination of soil moisture rate daily, than determined 85% field capacity, 70% field capacity, 60% field capacity and 45% field capacity, respectively.
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               Factor Function
Results indicated that drought stress motivated a significant reduction in all of the growth parameters and essential oil yield and percent. The highest values of growth parameters and essential oil percent and yield were observed under 100% field capacity (control). Also, the highest values of Mentone and menthofuran were obtained under 100% field capacity (control) and the highest values of menthol were obtained under 70% field capacity by using gas chromatography-mass spectroscopy (GC-MS).
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               Factor Part Location NP Content
 
100% Field Capacity (Control)
 Aerial parts Iran
NP Content: 6.35 %
 
85% Field Capacity
 Aerial parts Iran
NP Content: 3.7 %
 
70% Field Capacity
 Aerial parts Iran
NP Content: 3.58 %
 
60% Field Capacity
 Aerial parts Iran
NP Content: 5.3 %
 
45% Field Capacity
 Aerial parts Iran
NP Content: 2.22 %
 
0 mM NaCl (Control)
 Aerial parts Iran
NP Content: 11.67 %
 
50 mM NaCl
 Aerial parts Iran
NP Content: 6.37 %
 
100 mM NaCl
 Aerial parts Iran
NP Content: 6.04 %
  Factor Name: Month Variation [2]
              Species Info Factor Info
               Experiment Detail
The peppermint material was obtained from ten cultivation sites (four growers) around Le Mayetde-Montagne, Allier, France (altitude 400 to 800 m). The individual surface areas ranged from 0.6 to 2.5 ha for an overall surface of 8 to 10 ha. Planting density was 30,000 plants/ha.
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               Factor Function
A marked inversion of the menthol/menthone ratio was observed according to harvesting time. The late blooming period gave oils rich in menthol. A second harvest gave a high-quality oil and increased overall yield. Pre-drying did not affect the chemical composition of the oil obtained but allowed larger amounts of plant material to be distilled. In particular, Bouverat-Bernier showed an increase in oil yield up to flowering and a fall thereafter and an increase of levels of menthol and menthyl acetate while those of menthone decreased from June to September. For Hungarian peppermint, the levels of menthone were always greater than those of menthol regardless of harvest time.
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               Factor Part Location NP Content
 
Harvesting time: 14-June
 Whole plant Allier, France
NP Content: 0.1 %
 
Harvesting time: 5-July
 Whole plant Allier, France
NP Content: 0.2 %
 
Harvesting time: 29-July
 Whole plant Allier, France
NP Content: 0.7 %
 
Harvesting time: 15-August
 Whole plant Allier, France
NP Content: 3.7 %
 
Harvesting time: 15-September
 Whole plant Allier, France
NP Content: 3.4 %
 
Harvesting time: 30-September
 Whole plant Allier, France
NP Content: 0.8 %
 
Harvesting time: 30-October
 Whole plant Allier, France
NP Content: 0.4 %
      Species Name: Mentha Pulegium
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
The aerial parts of flowering Mentha pulegium plants (cut at ground level) and individual M. pulegium plants were collected in the summer (July, 2003) from three wild populations located in the Municipality of Laganas, Zakynthos, W. Greece. Location 1 (N 37° 41′ 29″, E 20° 50′ 25″; map datum WGS 84; altitude 3 m; 14/07/03) was close to Keri Beach (Limni Keriou), Location 2 (N 37° 43′ 34″, E 20° 50′ 41″; altitude 3 m; 13/07/03) was near the village of Kalamaki and Location 3 (N 37° 39′ 39″, E 20° 48′ 44″; altitude 160 m; 17/07/03) was near the village of Vasilikos. The three locations are within the mainland limits of the protected area of the National Marine Park of Zakynthos (NATURA 2000 Network, site GR 2210002; 14).
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               Factor Function
The composition of the inflorescence (I), leaf (L) and stem (S) essential oils of wild Mentha pulegium plants from three populations (1-3) on the island of Zakynthos were examined. Pulegone (32.8 %, S1 to 75.8 %, I3) was the major constituent of all of the oils. The other main constituents were piperitenone (5.1 %, L3 to 35 %, I2), isomenthone (4.3 %, I2 to 28.6 %, L3) and piperitone (0.5 %, I3 to 5.2 %, L2). In total, C-3-oxygenated p-menthane compounds constituted from 73.0 % (S1) to 96.2 % (I2) of the oils. The piperitenone content of the inforescence oils was up to 2.4 (Loc 3) times higher than that of the leaf oils. Correspondingly, the isomenthone content of the leaf oils was up to 4.2 (Loc 2) times higher than that of the inforescence oils. The ratio of the isomenthone:piperitenone content of the oils (n=3) was markedly different for the inforescence (mean 0.31), leaf (mean 2.91) and stem (mean 1.12) oils.
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               Factor Part Location NP Content
 
Inflorescence: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Inflorescence Zakynthos, Greece
NP Content: 0.1 %
 
Inflorescence: (Locality: near the village of Kalamaki, Zakynthos, Greece; Altitude 3 m)
 Inflorescence Zakynthos, Greece
NP Content: 0.1 %
 
Inflorescence: (Locality: near the village of Vasilikos, Zakynthos, Greece; Altitude 160 m)
 Inflorescence Zakynthos, Greece
NP Content: 0.1 %
 
Leaf: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Leaves Zakynthos, Greece
NP Content: 0.3 %
 
Leaf: (Locality: near the village of Kalamaki, Zakynthos, Greece; Altitude 3 m)
 Leaves Zakynthos, Greece
NP Content: 0.2 %
 
Leaf: (Locality: near the village of Vasilikos, Zakynthos, Greece; Altitude 160 m)
 Leaves Zakynthos, Greece
NP Content: 0.1 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Stems Zakynthos, Greece
NP Content: 0.9 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Stems Zakynthos, Greece
NP Content: 11.6 %
 
Stem: (Locality: near the village of Kalamaki, Zakynthos, Greece; Altitude 3 m)
 Stems Zakynthos, Greece
NP Content: 26 %
 
Stem: (Locality: near the village of Vasilikos, Zakynthos, Greece; Altitude 160 m)
 Stems Zakynthos, Greece
NP Content: 0.4 %
 
Stem: (Locality: near the village of Vasilikos, Zakynthos, Greece; Altitude 160 m)
 Stems Zakynthos, Greece
NP Content: 10.3 %
      Species Name: Mentha spicata
  Factor Name: Altitude Variation [4]
              Species Info Factor Info
               Experiment Detail
The aerial parts of flowering Mentha spicata plants (cut at ground level) and individual M. spicata plants were collected in the summer (July, 2003) from three wild populations located in the Municipality of Laganas, Zakynthos, W. Greece. Location 1 (N 37° 39′ 39″, E 20° 48′ 44″; map datum WGS 84; altitude 160 m; 14/07/03) was near the village of Keri, Location 2 (N 37° 41′ 29″, E 20° 50′ 25″; altitude 3 m; 14/07/03) was close to Keri Beach (Limni Keriou) and Location 3 (N 37° 43′ 34″, E 20° 50′ 41″; altitude 35 m; 14/07/03) was near the village of Pandocratoras. The three locations are within the mainland limits of the protected area of the National Marine Park of Zakynthos (NATURA 2000 Network, site GR 2210002; 8).
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               Factor Function
The main oil constituents were trans-piperitone oxide, piperitenone oxide and 1,8-cineole. On a whole plant basis (aerial parts) the trans-piperitone oxide content ranged from 1.4 % location (Loc 1) to 32.5% (Loc 3) and appeared to have an inverse relationship with the 1,8-cineole content which ranged from 10.8 % (Loc 3) to 37.9 % (Loc 1). 1,8-cineole was the major oil constituent (37.9 %) of M. spicata plants from Loc 1. The major constituent of the inflorescence oils was piperitenone oxide which ranged from 32.4 % (Loc 3) to 46.3 % of the oil (Loc 1). The major constituent of the leaf oils was 1,8-cineole (40.5 %) in plants from Loc 1 and trans-piperitone oxide in plants from Loc 2 (19.8 %) and Loc 3 (33.5 %). This is the first report for wild populations in Greece of a M. spicata oil in which 1,8-cineole is the major constituent. The observed variation in essential oil composition between locations and plant organs in July would not appear to be directly related to the climatic conditions.
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               Factor Part Location NP Content
 
Inflorescence: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
 Inflorescence Zakynthos, Greece
NP Content: 0.2 %
 
Inflorescence: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
 Inflorescence Zakynthos, Greece
NP Content: 0.2 %
 
Leaf: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
 Leaves Zakynthos, Greece
NP Content: 0.2 %
 
Leaf: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Leaves Zakynthos, Greece
NP Content: 0.1 %
 
Leaf: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
 Leaves Zakynthos, Greece
NP Content: 0.2 %
 
Stem: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
 Stems Zakynthos, Greece
NP Content: 0.5 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Stems Zakynthos, Greece
NP Content: 0.2 %
References
1 The effect of drought stress on growth parameters, essential oil yield and constituent of Peppermint (Mentha piperita L.)
2 Variation of the Chemical Composition of Essential Oil of Mentha piperita L. during the Growing Time
3 Differences Between The Inflorescence, Leaf And Stem Essential Oils Of Wild Mentha Pulegium Plants From Zakynthos, Greece
4 Mentha Spicata Essential Oils Rich In 1,8-Cineole And 1,2-Epoxy-P-Menthane Derivatives From Zakynthos (Ionian Island, W Greece)