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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14O
Molecular Weight 150.2179
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERILLALDEHYDE, (-)-

SMILES

C=C(C)[C@]1([H])CC=C(CC1)C=O

InChI

InChIKey=RUMOYJJNUMEFDD-SNVBAGLBSA-N
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H14O
Molecular Weight 150.2179
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Perillyl alcohol dehydrogenase from a soil pseudomonad.
1966 May 25
Microbiological transformations of terpenes. IX. Pathways of degradation of limonene in a soil pseudomonad.
1966 Sep
Carvone and perillaldehyde interfere with the serum-induced formation of filamentous structures in Candida albicans at substantially lower concentrations than those causing significant inhibition of growth.
2002 Jul
Synthesis of both enantiomers of isorobinal, a novel cyclic monoterpene isolated from the astigmatid mite, Rhizoglyphus sp.
2002 Nov
Bactericidal activities of plant essential oils and some of their isolated constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica.
2002 Oct
Monoterpene regulation of Ras and Ras-related protein expression.
2003 Jun
Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro.
2003 Oct 17
Antibacterial activities of naturally occurring compounds against antibiotic-resistant Bacillus cereus vegetative cells and spores, Escherichia coli, and Staphylococcus aureus.
2004 Aug
Essential oils: their antibacterial properties and potential applications in foods--a review.
2004 Aug 1
Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.
2004 Feb
Action of different monoterpenic compounds against Anisakis simplex s.l. L3 larvae.
2004 Jan
Study of the carbonyl products of terpene/OH radical reactions: detection of the 2,4-DNPH derivatives by HPLC-MS.
2004 Jun
Repellency of essential oils of some Kenyan plants against Anopheles gambiae.
2004 Oct
Kinetic mechanism for predicting secondary organic aerosol formation from the reaction of d-limonene with ozone.
2005 Dec 15
The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers.
2005 Feb
Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto.
2005 Mar
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
2005 May
Vasodilative effect of perillaldehyde on isolated rat aorta.
2005 May
Analysis by gas chromatography-mass spectrometry of the volatiles from the fruits of Ammodaucus leucotrichus subsp. leucotrichus and subsp. nanocarpus grown in North Africa and the Canary Islands, respectively.
2006 Mar 10
Antimicrobial effect of trans-cinnamaldehyde, (-)-perillaldehyde, (-)-citronellal, citral, eugenol and carvacrol on airborne microbes using an airwasher.
2006 Nov
Parectadial, a monoterpenoid from the defensive spray of Parectatosoma mocquerysi.
2007 Aug
The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity.
2008 Aug 11
Conformational flexibility in terpenes: vibrational circular dichroism (VCD), infrared and Raman study of S-(-)-perillaldehyde.
2008 Aug 28
Opposite stereochemical courses for enzyme-mediated alkene reductions of an enantiomeric substrate pair.
2008 Jun 18
Increasing antioxidant activity and reducing decay of blueberries by essential oils.
2008 May 28
Inhibitory activity of hydrosols, herbal teas and related essential oils against filament formation and the growth of Candida albicans.
2009
A nine-step total synthesis of (-)-platencin.
2009 Apr 17
Perillartine.
2009 Aug 15
Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens.
2009 Feb 15
Preliminary analysis on essential oil composition of Perilla L. cultivated in Lithuania.
2009 Jul-Aug
Fragrant unsaturated aldehydes elicit activation of the Keap1/Nrf2 system leading to the upregulation of thioredoxin expression and protection against oxidative stress.
2009 May
Chemical composition and antimicrobial activity of the extracts of Kefe cumin (Laser trilobum L.) fruits from different regions.
2009 Nov
Tumour-specific HMG-CoAR is an independent predictor of recurrence free survival in epithelial ovarian cancer.
2010 Apr 1
(S)-Perillaldehyde azine.
2010 Feb 6
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.
2010 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:49:39 UTC 2021
Edited
by admin
on Sat Jun 26 03:49:39 UTC 2021
Record UNII
5EL0Y7P6LP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERILLALDEHYDE, (-)-
Common Name English
L-PERILLALDEHYDE
Common Name English
(S)-(-)-PERILLIC ALDEHYDE
Common Name English
1-CYCLOHEXENE-1-CARBOXALDEHYDE, 4-(1-METHYLETHENYL)-, (4S)-
Systematic Name English
(-)-PERILLA ALDEHYDE
Common Name English
(S)-4-ISOPROPENYL-1-CYCLOHEXENE-1-CARBOXALDEHYDE
Systematic Name English
(S)-PERILLALDEHYDE
Common Name English
(4S)-P-MENTHA-1,8-DIEN-7-AL
Systematic Name English
PERILLALDEHYDE L-FORM [MI]
Common Name English
(-)-PERILLALDEHYDE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 115869
Created by admin on Sat Jun 26 03:49:39 UTC 2021 , Edited by admin on Sat Jun 26 03:49:39 UTC 2021
Code System Code Type Description
EPA CompTox
18031-40-8
Created by admin on Sat Jun 26 03:49:39 UTC 2021 , Edited by admin on Sat Jun 26 03:49:39 UTC 2021
PRIMARY
CAS
18031-40-8
Created by admin on Sat Jun 26 03:49:39 UTC 2021 , Edited by admin on Sat Jun 26 03:49:39 UTC 2021
PRIMARY
FDA UNII
5EL0Y7P6LP
Created by admin on Sat Jun 26 03:49:39 UTC 2021 , Edited by admin on Sat Jun 26 03:49:39 UTC 2021
PRIMARY
MERCK INDEX
M8552
Created by admin on Sat Jun 26 03:49:39 UTC 2021 , Edited by admin on Sat Jun 26 03:49:39 UTC 2021
PRIMARY Merck Index
PUBCHEM
2724159
Created by admin on Sat Jun 26 03:49:39 UTC 2021 , Edited by admin on Sat Jun 26 03:49:39 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Pure compound identified in the Paeonia lactiflora (Paeoniaceae) root steam distillate with growth-inhibiting activity against nine harmful intestinal bacteria and eight lactic acid-producing bacteria.