Details of Natural Product (NP)

General Information of Natural Product (ID: NP0259)
  Natural Product Name
Citronellal
  Synonyms
CITRONELLAL; 106-23-0; 3,7-Dimethyloct-6-enal; 3,7-Dimethyl-6-octenal; Rhodinal; 6-Octenal, 3,7-dimethyl-; 2,3-Dihydrocitral; Citronellel; beta-Citronellal; 3,7-Dimethyl-6-octen-1-al; (+/-)-Citronellal; CITRONELLOL,(D); .beta.-Citronellal; 8000-29-1; NSC 46106; CHEBI:47856; 3,7-dimethyl-oct-6-enal; NSC46106; MFCD00038090; Citronella; D-Rhodinal; 6-Octenal, 3,7-dimethyl-, (R)-; Rhodinal (VAN); Citronella (natural); FEMA No. 2307; HSDB 594; EINECS 203-376-6; AI3-00203; CCRIS 8421; beta -Citronellal; racemic citronellal; (RS)-citronellal; (+/-) citronellal; ( inverted exclamation markA)-Citronellal; 6-Octenal,7-dimethyl-; Epitope ID:112868; EC 203-376-6; DSSTox_CID_21790; DSSTox_RID_79843; DSSTox_GSID_41790; SCHEMBL29275; 3,7-dimethyloct-6-en-1-al; CHEMBL447944; GTPL6300; DTXSID3041790; FEMA 2307; (+/-)-3,7-Dimethyl-6-octenal; HY-N7126; Tox21_301195; c1026; NSC-46106; s5585; AKOS000121405; (+/-)-Citronellal, >=85%, FG; CCG-266248; CS-W010931; (+/-)-Citronellal, analytical standard; NCGC00248328-01; NCGC00255093-01; AS-54400; CAS-106-23-0; (+/-)-Citronellal, >=95.0% (GC); DB-040680; DB-072650; FT-0604386; FT-0623961; FT-0623963; FT-0699573; C17384; P50009; (+/-)-Citronellal, natural, >=85%, FCC, FG; A801397; J-502100; W-108770; Q61651085; Poly((1,3a,4,6,7,7a-hexahydro-1,3-dioxo-3H-furo(3,4-c)pyran-4,6-diyl)(tetrahydro-2,5-dioxo-3,4-furandiyl)methylene) (9CI); Poly[(1,4,6,7,7a-hexahydro-1,3-dioxo-3H-furo[3,4-c]pyran-4,6-diyl)(tetrahydro-2,5-dioxo-3,4-furandiyl)methylene]
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  Formula C10H18O
  Weight 154.25
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
  InChI Key NEHNMFOYXAPHSD-UHFFFAOYSA-N
  Isomeric SMILES CC(CCC=C(C)C)CC=O
  Canonical SMILES CC(CCC=C(C)C)CC=O
  External Links PubChem ID 7794
CAS ID 106-23-0
NPASS ID NPC276009
CHEMBL ID CHEMBL447944
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [1]
              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: 5.2 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
 Aerial parts Patagonia, Argentina
NP Content: 2.4 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
 Aerial parts Patagonia, Argentina
NP Content: 2.4 %
      Species Name: Cassinia laevis
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Six samples of Cassinia laevis R. Br. (coughbush, wild rosemary) were gathered from Lowood, 45 km west of Brisbane to Murphy's Creek area 100 km west of Brisbane, Australia from 1994 to 1998. Samples were identified by a LAEV prefix. LAEV 1 and LAEV 4 were collected from the roadside verge of the Gatton-Toowoomba bypass road (Lat. 27° 32′ 21″ S; Long. 152° 14′ 28″ E). LAEV 2 and LAEV 5 were collected from a different location in the same area (Lat. 27° 33′ 08″ S; Long. 152° 15′ 00″ E). LAEV 7 were collected from the Murphy's creek area (Lat. 27° 31′ 05″ S; Long. 152° 04′ 15″ E), growing on the roadside and in an adjacent paddock. Sample LAEV 9, was collected from the roadside area of the Warrego Highway (Lat. 27° 32′ 10″ S; Long. 152° 27′ 12″ E). The collected leaf and flower samples had aromas of trampled grass with a slight hint of curry.
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               Factor Function
Spathulenol was the major compound in flower oils (8-12%) compared to leaf oils (0.3-4.0%) which had ledol(37.5-53.6%) as the major compound.
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               Factor Part Location NP Content
 
Flower: Sample 1 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
 Flowers Brisbane, Queensland, Australia
NP Content: 0.4 %
 
Flower: Sample 4 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
 Flowers Brisbane, Queensland, Australia
NP Content: 0.7 %
 
Flower: Sample 2 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
 Flowers Brisbane, Queensland, Australia
NP Content: 0.6 %
 
Leaf: Sample 3 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
 Leaves Brisbane, Queensland, Australia
NP Content: 0.5 %
 
Leaf: Sample 6 (Locality: Murphy's creek area, Brisbane, Queensland)
 Leaves Brisbane, Queensland, Australia
NP Content: 0.9 %
 
Leaf: Sample 5 (Locality: roadside area of the Warrego Highway, Brisbane, Queensland)
 Leaves Brisbane, Queensland, Australia
NP Content: 0.3 %
      Species Name: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [3]
              Species Info Factor Info
               Experiment Detail
Four kinds of fresh sweet oranges were obtained in the same season, November 2000, in Guangzhou. Citrus sinensis var. Hongjiang (called 'hong jiang chen' in Chinese) and C. sinensis Osbeck var. Anliu (called 'luo gang chen') were obtained at an orchard in Luo gang in Guangzhou (25 km from the center of Guangzhou). Citrus sinensis var. Sihui (called 'sihui ju') was harvested at the Shigou Experimental Farm in Sihui City in Guangdong Province (75 km far away from Guangzhou). Citrus sinensis var. Washington navel (called 'qi chen') which was produced in Jiangxi Province (200 km from Guangzhou; bordering Guangdong Province), was purchased at the wholesale market in Guangzhou. All oranges were kept in a cold room until prepared a few days later.
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               Factor Function
The peel oil compositions of four kinds of sweet oranges in China, Citrus sinensis Osbeck var. Hongjian, C. sinensis Osbeck var. Anliu, C. sinensis Osbeck var. Sihui and C. sinensis Osbeck var. Washington navel, were investigated by GC and GC/MS. The essential oils were extracted by cold-pressing method. Forty-two to 53 compounds were quantitatively determined for each variety. Their percentages, respectively, were: > 97.3%, > 98.4%, > 97.5% and > 98.0% in hydrocarbons; > 1.5%, > 0.7%, > 0.8% and > 0.9% in total aldehydes; 0.8%, 0.5%, 0.5% and 0.5% in alcohols. Either cis-or trans-limonene oxide was detected in small amounts in each of the four samples, with Hongjiang containing both limonene oxides. delta-3-Carene was commonly quantified at a level of 0.1% in all the samples. The content of aliphatic aldehydes, including octanal, nonanal, decanal and dodecanal, exceeded that of terpene aldehydes, such as neral and geranial in Hongjiang (0.9%) and Washington navel (0.6%), whereas the aliphatic aldehydes in Anliu and Sihui were present to a lesser degree than the terpene aldehydes. Either alpha- or beta-sinensal was detected in trace amounts in each of the four samples. Linalool was the major alcohol in all the samples. Nootkatone was not detected.
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               Factor Part Location NP Content
 
Citrus sinensis var. Anliu
 Fruits China
NP Content: 0.1 %
 
Citrus sinensis var. Hongjiang
 Fruits China
NP Content: 0.1 %
 
Citrus sinensis var. Sihui
 Fruits China
NP Content: 0.1 %
 
Citrus sinensis var. Washington navel
 Fruits China
NP Content: > 0.005; < 0.05 %
      Species Name: Cymbopogon winterianus
  Factor Name: Pest Infestation [4]
              Species Info Factor Info
               Experiment Detail
General plantation of citronella cv. Java 2 was maintained following recommended agricultural practices at the Experimental Farm of Central Institute of Medicinal and Aromatic Plants, Field Station, Hyderabad, India. The experimental station has a semi-arid tropical climate. The experiment was conducted in the same plantation for 2 consecutive years during the summer month of June 1996 and 1997, when the incidence of the disease was higher. In each year, 12 each of healthy and diseased plants were selected at random and harvested. The occurrence of the disease is generally observed during the hot summer season months, when the temperatures are in the range 36-43 ℃. Initial symptoms of the pest attack appear as yellow specks or blotches, mostly along leaf margins, that in later stages develop into yellow streaks running along the length of the affected leaves. Emerging young leaves are pale green to yellow coloured, twisted, crinkled, developed into whip-like structures and in severe cases of infection fail to open. Even if they do open, these leaves fail to exhibit a smooth leaf surface. Severely affected older leaves turn brown, dry and die. The overall growth and development of the infected plant is severely affected, giving it a dwarfed and unhealthy appearance.
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               Factor Function
The essential oil examined by GC and GC-MS from cultivated healthy plants contained citronellal (28.4%), geraniol (24.8%), citronellol (11.8%) and elemol (10.2%). The major components from diseased plants were geraniol (19.0-25.5%), elemol (15.3-20.4%), citronellal (13.4-19.1%) and citronellol (12.9-15.1%). Caryophyllene oxide (3.5-6.0%) was an important minor component.
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               Factor Part Location NP Content
 
Healthy leaves of healthy plant
 Leaves Hyderabad, India
NP Content: 28.4 %
 
Healthy leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 19.1 %
 
Crinkled, whip like leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 19.1 %
 
Dead leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 13.4 %
 
Semi-diseased leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 17.2 %
      Species Name: Ducrosia anethifolia
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
The aerial parts of Ducrosia anethifolia (DC.) Boiss. were collected in the wild from Mehdi Abad (Kerman province, in southern Iran) at the flowering stage in June 2006. The material was dried at room temperature.
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               Factor Function
The 63 components of this interesting plant were identified in the oil of D. anethifolia, representing 94.0% of the oil. alpha-Pinene (11.6%), terpinolene(3.2%) and (z)-beta-ocimene (2.8%) were the main hydrocarbon components present in the oil, while decanal (54.0%), cis-chrysanthenyl acetate(3.2%) and decanoic acid (1.3%) were the major oxygen-containing constituents.
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               Factor Part Location NP Content
 
Locality: Larestan, Iran
 Aerial parts Iran
NP Content: 0.2 %
 
Locality: Karaj, Iran
 Aerial parts Iran
NP Content: 0.2 %
 
Locality: Kerman, Iran
 Aerial parts Iran
NP Content: 0.4 %
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [6]
              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 %
      Species Name: Micromeria biflora
  Factor Name: Seasonal Variation [7]
              Species Info Factor Info
               Experiment Detail
The aerial parts of M. biflora collected during November 1993 and June 1994 were used for the investigation.
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               Factor Function
The major constituents of the oil were neral (25.3-32.2%) and geranial (26.7-41.3%). The oil produced in the winter was found to contain higher amounts of oxygenated monoterpenes than the oil produced in the summer.
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               Factor Part Location NP Content
 
Harvesting time: Summer
 Aerial parts South India
NP Content: 0.08 %
 
Harvesting time: Winter
Aerial parts South India
NP Content: 0.1 %
      Species Name: Piper nigrum
  Factor Name: Cultivar Comparison; Harvest Time Variation [8]
              Species Info Factor Info
               Experiment Detail
The cultivars selected for this study are Sreekara, Vellanamban and one Indonesian cultivar Kutching grown in Kerala. These cultivars are commonly cultivated in the northern parts of Kerala. The fresh berries of the authenticated cultivars were collected from Indian Institute of Spices Research, Calicut and were dried in a cross flow drier at 45 ℃ and taken for the analysis.
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               Factor Function
The main components of vellanamban oil were sabinene (3.9-18.8%), beta-pinene (3.9-10.9%), limonene (8.3-19.8%) and beta-caryophyllene (28.4- 32.9%). Sreekara oil contained as major compounds beta-pinene (0-11.2%), limonene (20.1-22.1%) and beta-caryophyllene (16.8-23.1 %). Kutching oil contained alpha-pinene(2.3-5.4%), sabinene (6.7-13.3%), limonene (14.5-17.5%) and beta-caryophyllene (20.8-39.1%).
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               Factor Part Location NP Content
 
Piper nigrum cv. Kuching: (Harvesting time: 1991)
 Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1990)
 Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1991)
 Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1992)
 Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1990)
 Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1991)
 Berries India
NP Content: 0.1 %
References
1 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
2 Cassinia laevis R. Br. Flower and Leaf Essential Oils
3 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
4 Yellowing and crinkling disease and its impact on the yield and composition of the essential oil of citronella (Cymbopogon winterianus Jowitt.)
5 Chemical Composition of the Essential Oil of Ducrosia anethifolia (DC.) Boiss. from Kerman Province in Iran
6 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
7 Composition of the Essential Oil of Micromeria biflora
8 Studies on Essential Oil Composition of Cultivars of Black Pepper (Piper nigrum L.)-V