U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H16O
Molecular Weight 152.2334
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NERAL

SMILES

CC(C)=CCC\C(C)=C/C=O

InChI

InChIKey=WTEVQBCEXWBHNA-YFHOEESVSA-N
InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7-

HIDE SMILES / InChI
Molecular Formula C10H16O
Molecular Weight 152.2334
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

2010
474
PubMed

PubMed

TitleDatePubMed
Dual regulation of skin sensitizer-induced HMOX1 expression by Bach1 and Nrf2: Comparison to regulation of the AKR1C2-ARE element in the KeratinoSens cell line.
2015-11-01
Genes specifically modulated in sensitized skins allow the detection of sensitizers in a reconstructed human skin model. Development of the SENS-IS assay.
2015-06
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.
2015-03-01
Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans.
2013-12
A screen for disruptors of the retinol (vitamin A) signaling pathway.
2013-06
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.
2013-04
Retinoic acid biosynthesis catalyzed by retinal dehydrogenases relies on a rate-limiting conformational transition associated with substrate recognition.
2013-02-25
Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes.
2013-01-10
Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species.
2012-09-03
B cell increases and ex vivo IL-2 production as secondary endpoints for the detection of sensitizers in non-radioisotopic local lymph node assay using flow cytometry.
2012-03-25
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011-12
HPLC-FLD methods to quantify chloroaluminum phthalocyanine in nanoparticles, plasma and tissue: application in pharmacokinetic and biodistribution studies.
2011-08-25
The intra- and inter-laboratory reproducibility and predictivity of the KeratinoSens assay to predict skin sensitizers in vitro: results of a ring-study in five laboratories.
2011-04
Use of IL-8 release and p38 MAPK activation in THP-1 cells to identify allergens and to assess their potency in vitro.
2010-09
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.
2010-09
The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity.
2008-08-11
Effects of spice constituents on P-glycoprotein-mediated transport and CYP3A4-mediated metabolism in vitro.
2008-07
Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons.
2008-05-07
Retinoids during the in vitro transition from bovine morula to blastocyst.
2006-08
Analysis of the enzymatic formation of citral in the glands of sweet basil.
2006-04-15
Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol.
2005-07
Control of retinoic acid synthesis and FGF expression in the nasal pit is required to pattern the craniofacial skeleton.
2004-12-15
Assessment of estrogenic activity in some common essential oil constituents.
2002-11
Antifungal properties of essential oils and their main components upon Cryptococcus neoformans.
1994-12
Patents

Patents

04237072
2
06703527
7
08221736
2
JP2000053923A
3
JP2001114614A
3
JP2003245555A
2
JP2003529539A
2
JP2004123674A
11
JP2004123675A
11
JP2005239965A
2
JP2006006264A
2
JP2006290872A
5
JP2006510471A
3
JP2007063166A
2
JP2007282593A
3
JP2007302572A
2
JP2007525670A
150
JP2008280539A
3
JP2008297236A
2
JP2009139368A
2
JP2009280573A
2
JP2010254898A
4
JP2011240622A
2
JP2013209432A
2
JPH01294601A
8
JPH01311191A
5
JPH02117994A
4
JPH02275816A
5
JPH03127750A
2
JPH09309802A
2
JPH10120541A
3
JPH107511A
2
JPS5223014A
2
JPS56133280A
2
JPS6083544A
2
JPS6122037A
3
JPS62169741A
2
JPS6476815A
2
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:21 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:21 GMT 2025
Record UNII
8M466BQL1X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CITRAL NERAL
MI  
Preferred Name English
NERAL
Systematic Name English
CITRAL NERAL [MI]
Common Name English
CITRAL-B
Common Name English
CIS-CITRAL
Common Name English
CITRAL B
Common Name English
(2Z)-3,7-DIMETHYLOCTA-2,6-DIENAL
Systematic Name English
Code System Code Type Description
EVMPD
SUB62725
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-379-2
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
CHEBI
29020
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
RXCUI
1484865
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY RxNorm
DAILYMED
8M466BQL1X
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
MESH
C007076
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
CHEBI
16980
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
PUBCHEM
643779
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID60881216
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
MERCK INDEX
m3591
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY Merck Index
SMS_ID
100000134491
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
FDA UNII
8M466BQL1X
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
CAS
106-26-3
Created by admin on Mon Mar 31 18:24:21 GMT 2025 , Edited by admin on Mon Mar 31 18:24:21 GMT 2025
PRIMARY
Related Record Type Details
JAVA CITRONELLA OIL
PARENT -> CONSTITUENT MAY BE PRESENT
LEMON OIL, COLD PRESSED
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966