General Information of Natural Product (ID: NP0005)
  Natural Product Name
2-Phenylethanol
  Synonyms
2-PHENYLETHANOL; Phenethyl alcohol; Phenylethyl alcohol; Benzeneethanol; 60-12-8; Phenylethanol; Benzyl carbinol; Phenethanol; 2-Phenylethyl alcohol; 2-PHENYL-ETHANOL; beta-Phenylethanol; 2-Phenylethan-1-Ol; 2-Phenethyl alcohol; Benzylmethanol; Phenethylalcohol; Methanol, benzyl-; Benzenethanol; Benzylcarbinol; 2-Hydroxyethylbenzene; 1-Phenyl-2-ethanol; Ethanol, 2-phenyl-; 2-PEA; FEMA No. 2858; Phenyl ethyl alcohol; beta-Phenylethyl alcohol; beta-PEA; 2-Phenethanol; Hydroxyethylbenzene; UNII-ML9LGA7468; MFCD00002886; .beta.-Phenylethanol; .beta.-PEA; 1321-27-3; beta-Phenethyl alcohol; .beta.-Phenethyl alcohol; .beta.-Hydroxyethylbenzene; .beta.-Phenylethyl alcohol; Phenylethyl alcohol [USP]; ML9LGA7468; CHEBI:49000; NSC-406252; NCGC00166215-02; DSSTox_CID_6342; Phenylethyl alcohol (USP); DSSTox_RID_78104; DSSTox_GSID_26342; Caswell No. 655C; Phenyl Ethanol(Natural); FEMA Number 2858; beta-Fenylethanol; beta-Fenylethanol [Czech]; 2-phenyl ethanol; Ethanol, phenyl-; CAS-60-12-8; Phenethyl alcohol (natural); beta-Fenethylalkohol [Czech]; beta-Fenethylalkohol; PEL; SMR000059156; HSDB 5002; EINECS 200-456-2; EPA Pesticide Chemical Code 001503; NSC 406252; BRN 1905732; benzene-ethanol; Mellol; phenyl-ethanol; Benzyl-Methanol; AI3-00744; 2-PhenyIethanol; phenylethyl-alcohol; .beta.-Phenethanol; .beta.-Fenylethanol; b-Hydroxyethylbenzene; Benzyl ethyl alcohol; 2-phenyl-1-ethanol; Benzeneethanol, 9CI; betaphenylethyl alcohol; .beta.-Fenethylalkohol; 2-Phenylethanol, USP; Rose oil (Salt/Mix); A-PEA; beta -hydroxyethylbenzene; 2-Phenylethanol, 99%; .beta.-P.E.A.; Phenylethyl alcohol, USAN; bmse000659; Phenylethyl, beta- alcohol; EC 200-456-2; 2-(2-Hydroxyethyl)benzene; SCHEMBL1838; WLN: Q2R; .beta.-(hydroxyethyl)benzene; 4-06-00-03067 (Beilstein Handbook Reference); MLS001066349; MLS001336026; Phenethyl alcohol, 8CI, BAN; CHEMBL448500; PHENYLETHYL, B- ALCOHOL; DTXSID9026342; BDBM85807; FEMA 2858; HMS2093H05; HMS2233H06; HMS3374P04; Pharmakon1600-01505398; ZINC895934; BCP32115; CS-B1821; HY-B1290; NSC_6054; Tox21_113544; Tox21_201322; Tox21_303383; BBL036905; NSC406252; NSC759116; s3703; STL281950; 2-Phenylethanol, >=99.0% (GC); AKOS000249688; Tox21_113544_1; AS00558; CCG-213419; DB02192; MCULE-8439044075; NSC-759116; Phenethyl alcohol (Phenylethyl alcohol); CAS_60-12-8; Phenethyl alcohol, >=99%, FCC, FG; NCGC00166215-01; NCGC00166215-03; NCGC00166215-05; NCGC00257347-01; NCGC00258874-01; AC-18484; S992; SBI-0206858.P001; FT-0613332; FT-0673679; P0084; W6811; EN300-19347; C05853; D00192; D70868; Phenethyl alcohol, natural, >=99%, FCC, FG; AB00698274_05; A832606; Q209463; SR-01000763553; Phenylethyl alcohol;Phenethyl alcohol;Benzeneethanol; Q-200318; SR-01000763553-2; 0DE4CADC-AB8A-4038-BD6F-EBD009885652; F0001-1575; Z234896351; Phenylethyl alcohol, United States Pharmacopeia (USP) Reference Standard; Phenylethyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
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  Formula C8H10O
  Weight 122.16
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
  InChI Key WRMNZCZEMHIOCP-UHFFFAOYSA-N
  Isomeric SMILES C1=CC=C(C=C1)CCO
  Canonical SMILES C1=CC=C(C=C1)CCO
  External Links PubChem ID 6054
CAS ID 1960-12-08
NPASS ID NPC108218
HIT ID C0510
CHEMBL ID CHEMBL448500
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: phaseolorum sp. PR4
  Factor Name: PDB medium [1]
              Species Info Factor Info
               Experiment Detail
PR4 was isolated as an endophyte from the rhizome of Picrorhiza kurroa. Picrorhiza kurroa Royle ex. Benth (Plantaginaceae) is a perennial herb endemic to the north western alpine Himalayas. The endophyte PR4 was grown on PDA and in PDB at 26 ℃ for 15 days with constant shaking at 200 rpm in the latter case.
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               Mechanism
The two candidate NR-PKSs (PKS_3671 and PKS_4063) show differences in their domain organizations. PKS_3671 possesses two ACP-domains. Apart from that, only PKS_3671 contains a SAT-domain . These domains provide the first building block in the polyketide assembly, which usually is different from the extender unit malonyl-CoA (also known as the 'starter unit effect'). The ACA-synthesis however is believed to involve merely malonyl-CoA molecules. Even though the ACA-producing PKSs MdpG, ACAS, EncA, AptA and ClaG contain SAT-domains, an amino acid sequence alignment of these domains revealed that they all lack the active-site cysteine in the GXCXG motif and therefore most likely have no acyl transferase activity. Instead, all malonate building blocks are assumed to be loaded by the MAT. Under this aspect, the SAT-domain of PKS_3671 (that includes the correct GXCXG motif) likely incorporates a starter unit different from malonyl-CoA indicating that this enzyme is not involved in the biosynthesis of ACA. Therefore, the ACA-synthesizing PKS in C. asteris would rather be PKS_4063 that misses the SAT-domain .In the monodictyphenone and cladofulvin pathways, the cluster-encoded gene products MdpH and ClaH are crucial enzymes pushing the biosynthesis towards emodin. These EthD-domain-containing enzymes are suggested to catalyze the decarboxylation of ACA (3) into atrochrysone (4). Surprisingly, no such EthD-domain is encoded in the whole C. asteris genome. On the other hand, four genes directly attached to the putative ACA-synthase-coding gene pks_4063 show high similarity to genes of non-investigated PKS clusters in other fungi , which indicates an involvement in tailoring reactions of the respective polyketide pathways. According to InterProScan and BLASTp analyses, the genes sky_4060-62 encode a dehydratase and two dehydrogenases potentially catalyzing the multistep conversion of ACA (3) into emodin (1). Gene sky_4059 codes for a monooxygenase that putatively can connect two emodin molecules to the final product skyrin (2) in the style of the monooxygenase ClaM involved in the dimerization of the bisanthraquinone cladofulvin. Thus, the presence of these genes in the gene cluster gives further support to the hypothesis that PKS_4063 is the ACA-synthase in C. asteris. Mutational studies will be done in order to confirm these assumptions after a gene transfer system for this strain has been developed.
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               Factor Part Location NP Content
 
PDB medium (26℃ + 4 days)
Rhizomes Himalayas
NP Content: 54.6 % Relative area
      Species Name: Eugenia chlorophylla
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Plant material was collected at vegetative stage (stems and leaves,September 2005) and at flowering stage (leaves and flowers,December 2004), inCuritiba,Parana state, Brazil.
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               Factor Function
Thirty-four components were identified, representing more than 80% of total oil. The major components were beta-caryophyllene (flowers-12.8%), caryophyllene oxide (stems-17.2%), globulol (stems-16.5%; leaves-22.5% at vegetative stage and 18.9% at flowering stage), 1-epi-cubenol (stems-10.9%), epi-alpha-muurolol (stems-16.8%) and alpha-cadinol (stems-12.1%; flowers-10.1%).
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               Factor Part Location NP Content
 
Flower: flowering stage
Flowers Brazil
NP Content: 1.5 %
      Species Name: Rosa damascena
  Factor Name: Variety Comparison [3]
              Species Info Factor Info
               Experiment Detail
Experimental site: The present study was conducted at the experimental farm of the CSIR-Institute of Himalayan Bioresource Technology, Palampur (1325 m amsl, 32° 06′ 05″ N, 76° 34′10″ E), India, in 2011. Minimum temperature ranges from 3.5 ℃ to 19.8 ℃, maximum temperature ranges from 15.2 ℃ to 31.4 ℃, relative humidity varies between 62.2% and 94.1% in the morning and 45.0% and 87.2% in the evening, and bright sunshine hour ranges from 2.9 to 8.9 hours. Plant material: A population of approximately 50,000 plants raised from mixed stem cuttings collected from perennial rose plantations at the University of Agriculture, Udaipur, Rajasthan, India, and maintained in the field of the CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh, India, were utilized as an original gene pool of R. damascena. Two varieties, Jwala and Himroz were diversified through selections of desirable traits (morphological/oil content) across 25,000 plants. The five elites, three of R. damascena var. Jwala, (Indica, Super jwala and Jwala) and two of R. damascena var. Himroz (Hot himroz and Himroz) were developed through field selections and maintained at the Natural Plant Products Division Experimental Farm of the Institute. Rosa bourboniana plants were collected from the Fragrance and Flavour Development Centre, Kannauj, UP, India, during 1992 and maintained at the Natural Plant Products Division Experimental Farm of the Institute.
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               Factor Function
The essential oil content of the varieties of R. damascena varied from 0.037% to 0.051% and that of R. bourboniana was 0.017%. Super jwala recorded the highest oil content (0.051%). A total of 32 components were identified in the different varieties of rose oil. These components constituted 78.1-93.5% of the total rose oil species. The main components of rose oil were citronellol + nerol (16.3-30.1%), geraniol (15.8-29.3%), linalool (0.7-1.9%), rose oxide (0.9-2.6%), phenyl ethyl alcohol (0.1-0.4%), eugenol (0.3-2.2%), nonadecane (7.3-14.7%). The content of citronellol + nerol (30.1%) and geraniol (29.3%) was the highest in Himroz compared with other varieties.
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               Factor Part Location NP Content
 
Rosa damascena var. Himroz
Flowers India
NP Content: 0.1 %
 
Rosa damascena var. Hot Himroz
Flowers India
NP Content: 0.1 %
 
Rosa damascena var. Indica
Flowers India
NP Content: 0.2 %
 
Rosa damascena var. Jwala
Flowers India
NP Content: 0.1 %
 
Rosa damascena var. Super Jwala
Flowers India
NP Content: 0.1 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: <0.1 %
References
1 An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds
2 Chemical Composition and Antimicrobial Activity of Essential Oils of Eugenia chlorophylla (Myrtaceae)
3 Evaluation of several Rosa damascena varieties and Rosa bourboniana accession for essential oil content and composition in western Himalayas
4 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey