MOLECULE
(2E,6E)-Farnesol
Farnesol is a farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1. It has a role as an antimicrobial agent, a plant metabolite and a fungal metabolite. It is a primary alcohol, a polyprenol and a farnesane sesquiterpenoid.
Summary from ChEBI, via PubChem.
Identity
Chemistry
- Formula
- C15H26O
- Molecular weight
- 222.37 g/mol
- IUPAC name
- (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
- InChIKey
- CRDAMVZIKSXKFV-YFVJMOTDSA-N
- SMILES
- CC(=CCCC(=CCCC(=CCO)C)C)C
- PubChem
- CID 445070 ↗
Provenance
Contributing sources
- PubChem
- ChEBI
- LOTUS
Natural occurrence
Found in
- Tobacco 3
- A. hainanensis 2
- A. katsumadai 2
- Sweet wormwood 2
- Du Zhong 2
- Orange jasmine 2
- Guava 2
- Momi Fir 1
- A. oblongifolia 1
- B. cavipes 1
- Small garden bumblebee 1
- Wild cinnamon 1
- Papaya 1
- Roman Chamomile 1
- C. recutita 1
- C. deliciosa 1
- C. grandis 1
- Shaddock 1
- Mandarin orange 1
- C. geoides 1
- Lemonscented gum 1
- Zedoary 1
- Hops 1
- Common Juniper 1
- Lantana 1
- Japanese honeysuckle 1
- M. liliiflora 1
- Wild Chamomile 1
- Weeping Paperbark 1
- Horse Mint 1
- Spearmint 1
- Jasmine tobacco 1
- Korean ginseng 1
- Korean perilla 1
- Japanese Red Pine 1
- Japanese Black Pine 1
- P. fruticosus 1
- Cinquefoil 1
- Softhair coneflower 1
- Sandalwood 1
- S. spicatum 1
- Tomato 1
- S. aurantiaca 1
- S. cavipes 1
- Sweetscented marigold 1
- Hawaiian Fish Poisoning Plant 1
- Japanese torreya 1
- Caracus wigandia 1
- Z. zanthoxyloides 1
49 organisms, ranked by how many independent papers report the compound in each. Occurrence data from LOTUS, across 49 references.
Pharmacology
Protein interactions
-
Amine oxidase [flavin-containing] B Ki 0.8 uM
-
Amine oxidase [flavin-containing] B Ki 2.4 uM
-
cytochrome P450, family 2, subfamily C, polypeptide 19 Potency 4.4785 uM
-
cytochrome P450 family 2 subfamily C polypeptide 9 Potency 17.8293 uM
-
cytochrome P450 family 3 subfamily A polypeptide 4 Potency 25.1846 uM
-
cytochrome P450, family 1, subfamily A, polypeptide 2 Potency 28.2576 uM
-
Rap guanine nucleotide exchange factor 4 Potency 31.1984 uM
-
cytochrome P450 2D6 Potency 39.9149 uM
-
GLI family zinc finger 3 Potency 43.2771 uM
-
pregnane X nuclear receptor Potency 43.2771 uM
-
estrogen-related nuclear receptor alpha Potency 61.1306 uM
-
thyroid hormone receptor beta isoform 2 Potency 61.1306 uM
-
Nuclear factor (erythroid-derived 2)-like 2 Potency 68.5896 uM
-
retinoic acid nuclear receptor alpha variant 1 Potency 68.5896 uM
Laboratory measurements of the compound at its own doses. They do not describe any product that contains it.
Reported associations
Disease associations
-
Contact dermatitis, allergic Skin Disease
Associations recorded for the compound itself. A metabolomics association means it was detected or studied in that condition, not that it treats or causes it; an occupational entry describes a hazard of exposure. Neither is a therapeutic claim about any product.
Evidence
Literature
-
Acyclic sesquiterpenes released by Candida albicans inhibit growth of dermatophytes
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Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells
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Farnesol and farnesal dehydrogenase(s) in corpora allata of the tobacco hornworm moth, Manduca sexta
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New acyclic secondary metabolites from the biologically active fraction of Albizia lebbeck flowers