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Details

Stereochemistry RACEMIC
Molecular Formula C15H26O
Molecular Weight 222.3669
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NEROLIDOL, (6Z)-(+/-)-

SMILES

C=CC(C)(CC/C(/[H])=C(/C)\CCC=C(C)C)O

InChI

InChIKey=FQTLCLSUCSAZDY-KAMYIIQDSA-N
InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-

HIDE SMILES / InChI

Molecular Formula C15H26O
Molecular Weight 222.3669
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Nerolidol (aka peruviol) is a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers. Additionally, it is known for several biological activities including antioxidant, anti-fungal, anticancer, and antimicrobial activities.

CNS Activity

Curator's Comment:: referenced study was conducted in mouse

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Nerolidol effects on mitochondrial and cellular energetics.
2012 Mar
Assessment of anxiolytic effect of nerolidol in mice.
2016 Jul-Aug
[Construction of cell factories for high production of nerolidol in Saccharomyces cerevisiae].
2017 Aug
Nerolidol and its Pharmacological Application in Treating Neurodegenerative Diseases: A Review.
2018
Patents

Sample Use Guides

The essential oils Carvone, Eugenol, Geraniol, and Nerolidol are included in the viricidal spray AV2 in equal volumes diluted 50% in olive oil. The spray is topically administered to the cervix while the subject is in the lithotomic position and fitted with a speculum. Two pumps are administered with each pump delivering 100 micro-L of the solution.
Route of Administration: Vaginal
HepG2 cells were cultured in minimum essential medium (MEM) Eagle (with 2 mM L-glutamine and Earle's buffered saline solution (BSS) adjusted to contain 1.5 g/L sodium bicarbonate, 0.1 mM nonessential amino acids, and 1 mM sodium pyruvate), containing 10% fetal bovine serum. Cells were seeded in a 24-well plate and allowed to attach and recover for 1 day prior to drug treatment. Nerolidol was added at concentrations of 1.2 and 2.4 microM for proliferation assays and 10, 50, and 100 microM for cell viability assays. Cells were cultured for up o 3 days without media change or drug replenishment. At various time points, cells were washed, fixed and stained with sulforhodamine B to determine cell proliferation. Cytotoxicity of nerolidol was also evaluated through MTT assay. Nerolidol was toxic to HepG2 cells after 24 hours with a very strong inhibition of cell proliferation present even at the lowest concentrations tested (10 microM).
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:17:13 UTC 2021
Edited
by admin
on Sat Jun 26 13:17:13 UTC 2021
Record UNII
81K23DEF7B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEROLIDOL, (6Z)-(+/-)-
Common Name English
1,6,10-DODECATRIEN-3-OL, 3,7,11-TRIMETHYL-, (6Z)-
Systematic Name English
CIS-NEROLIDOL
Common Name English
NEROLIDOL CIS-FORM
MI  
Common Name English
NEROLIDOL CIS-FORM [MI]
Common Name English
NEROLIDOL, CIS-
Common Name English
Code System Code Type Description
EPA CompTox
3790-78-1
Created by admin on Sat Jun 26 13:17:13 UTC 2021 , Edited by admin on Sat Jun 26 13:17:13 UTC 2021
PRIMARY
MERCK INDEX
M7831
Created by admin on Sat Jun 26 13:17:13 UTC 2021 , Edited by admin on Sat Jun 26 13:17:13 UTC 2021
PRIMARY Merck Index
FDA UNII
81K23DEF7B
Created by admin on Sat Jun 26 13:17:13 UTC 2021 , Edited by admin on Sat Jun 26 13:17:13 UTC 2021
PRIMARY
ECHA (EC/EINECS)
223-263-5
Created by admin on Sat Jun 26 13:17:13 UTC 2021 , Edited by admin on Sat Jun 26 13:17:13 UTC 2021
PRIMARY
CAS
3790-78-1
Created by admin on Sat Jun 26 13:17:13 UTC 2021 , Edited by admin on Sat Jun 26 13:17:13 UTC 2021
PRIMARY
PUBCHEM
5320128
Created by admin on Sat Jun 26 13:17:13 UTC 2021 , Edited by admin on Sat Jun 26 13:17:13 UTC 2021
PRIMARY