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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H16O
Molecular Weight 152.2334
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERILLA ALCOHOL

SMILES

CC(=C)[C@H]1CCC(CO)=CC1

InChI

InChIKey=NDTYTMIUWGWIMO-SNVBAGLBSA-N
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H16O
Molecular Weight 152.2334
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Perilla alcohol is a naturally occurring monoterpene related to limonene. It is isolated from the essential oils of lavender, peppermint, spearmint, cherries, celery seeds, and several other plants. It has been used topically as a mosquito repellant and in toiletries and may be touted as a constituent of natural products such as tart cherry juice. Perillyl alcohol has demonstrated antiangiogenesis and anticancer effects in vitro. Purported mechanism of action is suppression of the synthesis of small G proteins, including RAS, thereby arresting tumor cells in the G1 phase of the cell cycle. Early clinical studies did not efficacy in prostate, ovarian or breast cancer, probably due to bad pharmacokinetic properties and toxicity after oral administration. More recent preliminary studies found intranasal delivery in patients with malignant gliomas to be well-tolerated and effective, with one study reporting tumor size regression, and another reporting increased overall survival and no side effects after long-term use.

Approval Year

PubMed

PubMed

TitleDatePubMed
Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin.
2010-01
Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol.
2009-12
Statin-induced muscle damage and atrogin-1 induction is the result of a geranylgeranylation defect.
2009-09
Perillyl alcohol attenuates Ras-ERK signaling to inhibit murine skin inflammation and tumorigenesis.
2009-05-15
Components of lemon essential oil attenuate dementia induced by scopolamine.
2009-04
GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data.
2009-02-24
[Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies].
2009-02
High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats.
2008-12-01
Sensitive determination of monoterpene alcohols in urine by HPLC-FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates.
2008-11-15
Fragrance material review on p-mentha-1,8-dien-7-ol.
2008-11
Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol.
2008-09-15
Gateways to clinical trials.
2008-09
Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas.
2008-09
PatternLab for proteomics: a tool for differential shotgun proteomics.
2008-07-21
Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.
2008-07-15
Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis.
2008-07
A pilot study of perillyl alcohol in pancreatic cancer.
2008-06-15
Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer.
2008-06
Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells.
2008-05-30
Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma.
2008-05-19
Ras pathway activation in gliomas: a strategic target for intranasal administration of perillyl alcohol.
2008-02-04
Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol.
2008
Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds.
2008
Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer.
2008
Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model.
2007-12
Rab-small GTPases are involved in fluvastatin and pravastatin-induced vacuolation in rat skeletal myofibers.
2007-12
Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells.
2007-11-18
Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor cells.
2007-09-01
Cloning of four genes involved in limonene hydroxylation from Enterobacter cowanii 6L.
2007-07
Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and farnesol is mediated by p21(Cip1) and p27(Kip1) in human pancreatic adenocarcinoma cells.
2007-03
Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review.
2006-12
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.
2006-08
Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells.
2006-06-01
Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells.
2006-05-18
Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549.
2006
In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression.
2006
Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis.
2006
Apocynin derivatives interrupt intracellular signaling resulting in decreased migration in breast cancer cells.
2006
Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells.
2006
Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol.
2006
Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway.
2005-09-15
Regio- and stereoselective fungal oxyfunctionalisation of limonenes.
2005-07-27
Gateways to clinical trials.
2005-06
Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells.
2005-05
Effect of D-limonene on immune response in BALB/c mice with lymphoma.
2005-05
Cancer preventive role of selected dietary factors.
2005-04-05
An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation.
2005-03-09
Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto.
2005-03
Terpenoids as plant antioxidants.
2005
Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo.
2005
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:01:06 GMT 2025
Edited
by admin
on Mon Mar 31 22:01:06 GMT 2025
Record UNII
3UL4QIY642
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEO-100
Preferred Name English
PERILLA ALCOHOL
Common Name English
(S)-(-)-PERILLYL ALCOHOL
Common Name English
(-)-PERILLA ALCOHOL
Common Name English
PERYCOROLLE
Common Name English
(-)-P-MENTHA-1,8-DIEN-7-OL
Systematic Name English
(S)-PERILLYL ALCOHOL
Common Name English
NEO100
Code English
1-CYCLOHEXENE-1-METHANOL, 4-(1-METHYLETHENYL)-, (4S)-
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 453314
Created by admin on Mon Mar 31 22:01:06 GMT 2025 , Edited by admin on Mon Mar 31 22:01:06 GMT 2025
Code System Code Type Description
PUBCHEM
369312
Created by admin on Mon Mar 31 22:01:06 GMT 2025 , Edited by admin on Mon Mar 31 22:01:06 GMT 2025
PRIMARY
CHEBI
15420
Created by admin on Mon Mar 31 22:01:06 GMT 2025 , Edited by admin on Mon Mar 31 22:01:06 GMT 2025
PRIMARY
CAS
18457-55-1
Created by admin on Mon Mar 31 22:01:06 GMT 2025 , Edited by admin on Mon Mar 31 22:01:06 GMT 2025
PRIMARY
FDA UNII
3UL4QIY642
Created by admin on Mon Mar 31 22:01:06 GMT 2025 , Edited by admin on Mon Mar 31 22:01:06 GMT 2025
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.
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY