Details of Natural Product (NP)

General Information of Natural Product (ID: NP0267)
  Natural Product Name
Cedrol
  Synonyms
Cedrol; (+)-Cedrol; 77-53-2; alpha-Cedrol; 8betaH-Cedran-8-ol; (8R)-cedran-8-ol; UNII-63ZM9703BO; MFCD00062952; CHEMBL1974890; CHEBI:10217; 63ZM9703BO; NSC403883; [3R-(3alpha,3abeta,6alpha,7beta,8aalpha)]-octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol; a-Cedrol; Cedrol (natural); Cedarwood oil alcohols; .alpha.-Cedrol; cedar camphor; 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-; (3R-(3alpha,3Abeta,6alpha,7beta,8aalpha))-octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol; 8.beta.H-Cedran-8-ol; Cedrol (6CI,7CI); EINECS 201-035-6; NSC 403883; Cedorol; Cedrol Crystals; AI3-02178; 1H-3a, octahydro-3,6,8,8-tetramethyl-, [3R-(3.alpha.,3a.beta.,6.alpha.,7.beta.,8a.alpha.)]-; Cedrol, redistilled; cedrol-(+); (+)-Cedryl alcohol; DSSTox_CID_21269; DSSTox_RID_79672; DSSTox_GSID_41269; SCHEMBL107488; (7beta,8alpha)-cedran-8-ol; 8betaH-Cedran-8-ol (8CI); 8-betaH-Cedran-8-ol (8CI); DTXSID1041269; HSDB 8265; (+)-Cedrol, analytical standard; HY-N2071; NSC46153; ZINC3978626; Tox21_202945; BDBM50430739; NSC-46153; s4938; (1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undecan-8-ol; AKOS024319138; CCG-266739; LMPR0103690007; NSC-403883; CAS-77-53-2; NCGC00260491-01; AC-34891; AS-13700; NCI60_003818; CS-0018576; FT-0623526; C09631; J10131; 062C952; A865207; (+)-Cedrol, >=99.0% (sum of enantiomers, GC); Q1052617; (3R,3aS,6R,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-ol; [3R-(3alpha,3abeta,6alpha,7beta,8aalpha)]-Octa-hydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
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  Formula C15H26O
  Weight 222.37
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
  InChI Key SVURIXNDRWRAFU-OGMFBOKVSA-N
  Isomeric SMILES C[C@@H]1CC[C@@H]2[C@]13CC[C@@]([C@H](C3)C2(C)C)(C)O
  Canonical SMILES CC1CCC2C13CCC(C(C3)C2(C)C)(C)O
  External Links PubChem ID 65575
CAS ID 77-53-2
NPASS ID NPC32222
CHEMBL ID CHEMBL1974890
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
 Aerial parts India
NP Content: 0.1 %
 
Artemisia annua cv. Jeevanraksha
 Aerial parts India
NP Content: 0.2 %
      Species Name: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [2]
              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. Hongjiang
 Fruits China
NP Content: < 0.005 %
      Species Name: Cupressus sempervirens
  Factor Name: Month Variation [3]
              Species Info Factor Info
               Experiment Detail
The leaves of C. sempervirens were collected in the region of central Dalmatia (Croatia) within 12 months (1999).
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               Factor Function
The oils produced in the autumn (September and October) were found to contain higher amounts of alpha-pinene (71.0% and 79.2%) than the oils produced from February to May (28.4-32.5%). The smallest amount of alpha-pinene (28.4%) was recorded in February, at the same time as the amount of cedrol, the quantitatively most important oxygenated compound, reached its maximum (12.9%).
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               Factor Part Location NP Content
 
Harvesting time: January
 Leaves Dalmatia, Croatia
NP Content: 3.6 %
 
Harvesting time: February
 Leaves Dalmatia, Croatia
NP Content: 12.9 %
 
Harvesting time: March
 Leaves Dalmatia, Croatia
NP Content: 8.5 %
 
Harvesting time: April
 Leaves Dalmatia, Croatia
NP Content: 8.8 %
 
Harvesting time: May
 Leaves Dalmatia, Croatia
NP Content: 10.6 %
 
Harvesting time: June
 Leaves Dalmatia, Croatia
NP Content: 3.5 %
 
Harvesting time: July
 Leaves Dalmatia, Croatia
NP Content: 3.2 %
 
Harvesting time: August
 Leaves Dalmatia, Croatia
NP Content: 6.9 %
 
Harvesting time: September
 Leaves Dalmatia, Croatia
NP Content: 1.2 %
 
Harvesting time: October
 Leaves Dalmatia, Croatia
NP Content: 1.4 %
 
Harvesting time: November
 Leaves Dalmatia, Croatia
NP Content: 5.8 %
 
Harvesting time: December
 Leaves Dalmatia, Croatia
NP Content: 4.2 %
      Species Name: Ferulago angulata
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Fresh F.angulata were leaves gathered and air dried in May, 2004 and the seeds collected in October, 2004 from both habitats (Shahoo and Nevakoh Mountains), Kermanshah Province western Iran.
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               Factor Function
The oil yield from seed was 5-fold that from leaves (3.2%/100g compared to 0.63%/100g). Cis-ocimene was the major constituent of the seed oil from both regions (64.8% and 76.11%) and a prominent constituent (>20% of the total oil) of the leaf oils of both habitats. alpha-Pinene was the next main component (7-27%) of all 4 oils. Seed oils, with one major component (cis-ocimene), differed from the leaf oils, which were composed mostly of 3 components (alpha-pinene, cis-ocimene, & germacrene D). Distinctions between the oils of the two habitats were less marked than the leaf-oil/seed-oil differences; the cis-ocimene content was higher and alpha-pinene was less in both seedand leaf-oils of the Shahoo habitats than the Nevakoh ecotype; trans-verbenol was absent from the Shahoo leaves, but reached a content of 5.8% in Nevahoh leaf-oil. Further distinctions were found in the content/presence/absence of 20-30 minor components of the oils.
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               Factor Part Location NP Content
 
Leaf: (Locality: Nevakoh Mountains, Kermanshah Province, western Iran)
 Leaves Iran
NP Content: 0.5 %
      Species Name: Juniperus thurifera
  Factor Name: Altitude Variation; High Temperature Treatment [5]
              Species Info Factor Info
               Experiment Detail
The plant materials were collected for P1: 2900 m, Ait Akak, Oukaimden, Atlas Mts, Morocco, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 12/12/2003; P2, 2200 m, Plateau of Matat, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 18/03/2003; P3: 2000 m, Foret Islane, Oukaimden, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns,12/12/2003. A portion of the leaves from each of the three trees (per population) were air dried for 16 days at room temperature (ca. 22 &#8451) to produce the dried leaf samples.
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               Factor Function
The oil yields from fresh leaves showed on differences among geographical sources. Air dried leaves appeared to yield more oil at the highest elevation (1.03%, Ait Lkak, 2900 m) than lower sites (0.67%, Plateau of Matat, 2200 m; 0.57%, Foret Islane, 2000 m). The essential oils from each geographic site had very similar composition in fresh versus air dried leaves. The essential oils from provenance Ait Lkak and Plateau of Matat were very similar and characterized by a high sabinene content (21.2, 35.9%), in contrast to 10.% sabinene from the provenance Foret Islane. The oil from Foret Islane had a high delta-cadinene content with 12.7%, whereas Aik Akak and Plateau of Matat contained only 0.6 and 0.8%.
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               Factor Part Location NP Content
 
Fresh leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
 Fresh leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.6 %
 
Fresh leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
 Fresh leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.5 %
 
Dry leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
 Dry leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: 1.1 %
 
Dry leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
 Dry leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.7 %
 
Dry leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
 Dry leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.4 %
 
Fresh leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
 Fresh leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.4 %
      Species Name: Piper nigrum
  Factor Name: Cultivar Comparison; Harvest Time Variation [6]
              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: 1990)
 Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1990)
 Berries India
NP Content: 0.3 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1991)
 Berries India
NP Content: 0.2 %
 
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: 0.6 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1992)
 Berries India
NP Content: 0.1 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
3 Seasonal Variation in Essential Oil Compositions of Cupressus sempervirens L.
4 The constituents of essential oils of Ferulago Angulata (SCHLECHT.) BOISS at two different habitals, Nevakoh and Shahoo, Zagross mountain, western Iran
5 Effect of the Leaf Drying and Geographic Sources on the Essential Oil Composition of Juniperus thurifera L. var. Africana Maire from the Tensift-Al Haouz, Marrakech Region
6 Studies on Essential Oil Composition of Cultivars of Black Pepper (Piper nigrum L.)-V