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Germacrene information


Germacrene A
Names
IUPAC name
(1E,5E,8S)-1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene
Other names
  • (−)-Germacrene A
  • (E,E)-Germacra-3,9,11-triene
  • (1E,5E,8S)-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
  • (S-(E,E))-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
Identifiers
CAS Number
  • 28387-44-2 checkY
  • B: 15423-57-1
  • C: 34323-15-4
  • D: 37839-63-7
3D model (JSmol)
  • Interactive image
  • A: Interactive image
  • B: Interactive image
  • C: Interactive image
  • E: Interactive image
Beilstein Reference
 6500908 (A) 1864177 (D)
ChEBI
  • A: CHEBI:36517
  • B: CHEBI:5337
  • C: CHEBI:61478
  • D: CHEBI:49045
ChEMBL
  • B: ChEMBL448125
ChemSpider
  • 29776407 ☒N
  • A: 7827628
  • B: 4444852
  • D: 28288426
KEGG
  • A: C16141
  • B: C09672
  • C: C19747
PubChem CID
  • A: 9548705
  • B: 5281519
  • C: 25244915
  • D: 5373727
  • E: 10632030
InChI
  • InChI=1S/C15H26/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,12,15H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+/t15-/m0/s1 ☒N
    Key: YDLBHMSVYMFOMI-SDFJSLCBSA-N ☒N
  • InChI=1/C15H26/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,12,15H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+/t15-/m0/s1
    Key: YDLBHMSVYMFOMI-SDFJSLCBBV
  • A: InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,15H,1,5,7-8,10-11H2,2-4H3/b13-6+,14-9+/t15-/m1/s1
    Key: XMRKUJJDDKYUHV-DFSVIBJJSA-N
  • D: InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-
    Key: GAIBLDCXCZKKJE-BZXLUOIMSA-N
  • E: InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,11,14-15H,1,5,7-8,10H2,2-4H3/b11-9+,13-6+
    Key: OAOGSSAAVUPEKA-BMCYRRRCSA-N
SMILES
  • C/C/1=C\CC/C(=C/C[C@H](CC1)C(C)C)/C
  • A: C/C/1=C\CC/C(=C/C[C@@H](CC1)C(=C)C)/C
  • B: C/C/1=C\CC/C(=C/CC(=C(C)C)CC1)/C
  • C: C/C/1=C\CC/C(=C/C=C(\CC1)/C(C)C)/C
  • E: CC\1CC/C=C(/CCC(/C=C1)C(=C)C)\C
Properties
Chemical formula
 C15H24
Molar mass 204.35 g/mol
Density 0.793 g/mL
Boiling point 236.4 °C (457.5 °F; 509.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Germacrene D
Names
IUPAC name
(S,1Z,6Z)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene
Other names
1-methyl-5-methylene-8-(1-methylethyl)-1,6-cyclodecadiene
Identifiers
CAS Number
  • 37839-63-7
3D model (JSmol)
  • Interactive image
ChemSpider
  • 28288426
PubChem CID
  • 5373727
InChI
  • InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-/t15-/m0/s1
    Key: GAIBLDCXCZKKJE-ACWLMNNXSA-N
  • InChI=1/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-/t15-/m0/s1
    Key: GAIBLDCXCZKKJE-ACWLMNNXBY
SMILES
  • C/C/1=C/CCC(=C)/C=C\[C@@H](CC1)C(C)C
Properties
Chemical formula
 C15H24
Molar mass 204.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Germacrenes are a class of volatile organic hydrocarbons, specifically, sesquiterpenes. Germacrenes are typically produced in a number of plant species for their antimicrobial and insecticidal properties, though they also play a role as insect pheromones. Two prominent molecules are germacrene A and germacrene D.

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Germacrene

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Germacrenes are a class of volatile organic hydrocarbons, specifically, sesquiterpenes. Germacrenes are typically produced in a number of plant species...

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Germacrene A hydroxylase

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Germacrene A hydroxylase (EC 1.14.13.123) is an enzyme with systematic name (+)-germacrene-A,NADPH:oxygen oxidoreductase (12-hydroxylating). This enzyme...

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Ocimum tenuiflorum

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are camphor (32%), eucalyptol (19%), ⍺-bisabolene (17%), eugenol (14%), germacrene (11%) and β-bisabolene (11%).[better source needed] In addition, more...

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Germacrene C synthase

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Germacrene C synthase (EC 4.2.3.60) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase (germacrene-C-forming). This enzyme...

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Absinthin

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terminal allylic carbon via Germacrene A hydroxylase, a cytochrome P450 enzyme. Oxidation of alcohol to aldol, via -germacrene A hydroxylase. Hydroxylation...

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Patchouli

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boiling the dried leaves and fermenting them for a period of time is best. Germacrene-B Patchoulol Norpatchoulenol The heavy, strong, woody, and earthy scent...

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Costunolide

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cyclase, (+)-germacrene A synthase, to form compound 2, (+)-germacryl cation. Inside this same enzyme, a proton is lost to form 3, (+)-germacrene A. The isoprenyl...

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Tobacco

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animals. Despite containing enough nicotine and other compounds such as germacrene and anabasine and other piperidine alkaloids (varying between species)...

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Geosmin

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(2006). "Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin". Journal of the American...

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Betel

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a major component of Sri Lankan Piper betle. Eugenol, isoeugenol, and germacrene D are other dominant compounds in other chemotypes. Leaves also contain...

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Cananga odorata

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various grades of ylang-ylang essential oil are reported as: Linalool Germacrene Geranyl acetate Caryophyllene p-Cresyl methyl ether Methyl benzoate Sesquiterpenes...

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Germacradienol synthase

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Germacradienol synthase (EC 4.2.3.22, germacradienol/germacrene-D synthase, 2-trans,6-trans-farnesyl-diphosphate diphosphate-lyase [(1E,4S,5E,7R)-germacra-1(10)...

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Oregano

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compounds include p-cymene, γ-terpinene, caryophyllene, spathulenol, germacrene D, β-fenchyl alcohol and δ-terpineol. Drying of the plant material affects...

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Osmeterium

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β-phellandrene, (Z)-ocimene, (E)-ocimene, β-caryophyllene, (E)-β-farnesene, and germacrene A, as well as a number of unidentified sesquiterpenoids. and that of its...

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Germacrene A alcohol dehydrogenase

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Germacrene A alcohol dehydrogenase (EC 1.1.1.314) is an enzyme with systematic name germacra-1(10),4,11(13)-trien-12-ol:NADP+ oxidoreductase. This enzyme...

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Stachys byzantina

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are rich in 1.8-cineole (14.8 %), linalool (12.9 %), cubenol (9.9 %), germacrene-D (9.6 %), α-terpineol (7.8 %), menthone (6.9 %) and (Z)-lanceol acetate...

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Lavender oil

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Terpenes / Sesquiterpenes β-Caryophyllene 4.62% 2.10% β-Farnesene 2.73% Germacrene 0.27% α-Humulene 0.28% Ketones Camphor 0.85% 13.00 % 3-Octanone 0.72%...

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Salvia leucantha

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sesquiterpene hydrocarbons ; β-caryophyllene, α-guaiene, cis-muurola-3,5-diene, germacrene D, and bicyclogermacrene. Bornyl acetate constituted 23.9% of the oil...

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Lamium purpureum

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British Isles. The essential oil is characterized by its high contents of germacrene D. The seed oil contains 16% of an acid characterized as (−)-octadeca-5...

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Aristolochia grandiflora

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essential oils include α-phellandrene and linalool from the stems and roots; germacrene D and γ-elemene from the leaves; and trans-nerolidol and geraniol from...

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Eleutherococcus senticosus

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Eleutherococcus senticosus include α-bisabolol (26%), β-caryophyllene (7%), germacrene D (7%), β-bisabolene (5%), and α-humulene (4%). Extracts from the root...

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Thujone

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"Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae)". Phytochemistry...

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Santonin

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cyclization of farnesyl diphosphate (FPP) to (+)-germacrene A by a sesquiterpene synthase. (+)-germacrene A hydroxylase then hydroxylates the isopropenyl...

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Piper cubeba

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sesquiterpenes (caryophyllene, copaene, α- and β-cubebene, δ-cadinene, germacrene), the oxides 1,4- and 1,8-cineole and the alcohol cubebol. About 15% of...

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