beta-Cubebene → Germacrene C

HRID 1386896Notes

Reaction equation

HRID 1386896 reaction equation
[CH3:1][C:2]1=[CH:3][CH2:4][C:5]([CH3:15])([CH3:14])[CH:6]=[CH:7][CH2:8][C:9]([CH3:13])=[CH:10][CH2:11][CH2:12]1.C[C@H]1[C@@]23CCC(=C)[C@@H]2[C@H]3[C@H](C(C)C)CC1.CC1[C@@H]2C[C@H](C(C)=C)CC[C@@]2(C)CCC=1.CC1C2CC(CCC2(C)CCC=1)=C(C)C.CC1CCC2[C@H]([C@H](C(C)C)CCC=2C)C=1.C[C@@H]1C2CC[C@H](C)C=2C[C@H](C(C)=C)CC1>>[CH3:13][C:9]1=[CH:10][CH2:11][CH2:12][C:2]([CH3:1])=[CH:3][CH:4]=[C:6]([CH:5]([CH3:14])[CH3:15])[CH2:7][CH2:8]1

Participants

7

Reactant 6

HCID 93081beta-CubebeneHCID 441005(+)-d-CadineneHCID 5222962-Isopropylidene-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthaleneHCID 5281520alpha-HumuleneHCID 5317844alpha-GuaieneHCID 10856614alpha-Selinine

Product 1

HCID 25244915Germacrene C

Procedure

The sources of authentic terpene standards were as follows: α-longipinene, cyclosativene, sativene and α-ylangene were from Abies balsamea oleoresin; δ-selinene was from Abies alba oleoresin, α-, β-, and γ-himachalene, α-and δ-amorphene, α-muurolene, guaia-6,9-diene, α-cadinene, δ-selinene, germacrene A, β-ylangene, β-longipinene, E-α-and β-bisabolene were (lifts from Larry Cool (University of California, Berkeley); germacrene B, and black pepper oleoresin containing α-cubebene and α-copaene, were gifts from Robert Adams (Baylor University); γ-humulene was from allspice seeds and as a gift from Ron Binder (USDA, Albany, Calif.); sibirene and longicyclene were from Pinus sibirica oleoresin; longifolene was purchased from Sigma Chemical Co.; E-α-larnesene was from parsley leaf oil; germacrene D was from the essential oil of caraway and Nepeta mussini; β-caryophyllene was a gift from Rudolf Hopp (Haarmann and Reimer GmbH); γ-bisabolene was isolated from carrot roots; α-humulene was purchased from Fluka Chemical Co.; β-cubebene was from the essential oil of Valencia orange peels; α-selinene and seli-3,7 (11)-diene were from celery seed, δ-cadinene was a gift from Margaret Essenberg (Oklahoma State University); α-guaiene was from patchouli essential oil; germacrene C was isolated from tomato leaf oil; bicyclogermacrene was from the essential oil of marjoram; and β-gurjunene was from ginger root. All other biochemicals and reagents were purchased from Sigma Chemical Co. or Aldrich Chemical Co., unless otherwise noted.

Sources & evidence

ORD record
ord-7e7357dc68564ed68e0121179d54a0ac
Source dataset
uspto-grants-2001_07
Patent number
US06265639B1

Reaction notes

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