Germacrene

Germacrenes are a group of five naturally occurring volatile organic hydrocarbons of the sesquiterpene and cycloalkene class. 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.

Germacrenes

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 Y 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 YN ?) Infobox references

Structures

Germacrene has five isomers.

Germacrene isomers

Germacrene A	Germacrene B	Germacrene C	Germacrene D	Germacrene E

Natural occurrences

The essential oils of deadnettles (genus Lamium),^[1] hedgenettles (genus Stachys),^[2] and Clausena anisata are characterized by their high contents of germacrene D. Germacrene B is a major component of patchouli oil.^[3]