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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H16O
Molecular Weight 152.2338
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERILLA ALCOHOL

SMILES

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

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 152.2338
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
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.
2000 Jan-Feb
Breast cancer chemoprevention: beyond tamoxifen.
2001
Biotransformation of limonene by Pseudomonas putida.
2001 May
Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans.
2002
Antileukemia activity of perillyl alcohol (POH): uncoupling apoptosis from G0/G1 arrest suggests that the primary effect of POH on Bcr/Abl-transformed cells is to induce growth arrest.
2002 Feb
Weight-loss drugs and supplements: are there safer alternatives?
2002 Jan
Induction of cytostasis in mammary carcinoma cells treated with the anticancer agent perillyl alcohol.
2002 Jan
Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine.
2002 Nov 25
Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention.
2002 Nov-Dec
Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer.
2003 Aug
A phase I trial of perillyl alcohol in patients with advanced solid tumors.
2003 Jun
Phase I trial of perillyl alcohol administered four times daily continuously.
2003 Nov
Effect of antiproliferative agents on vascular function in normal and in vitro balloon-injured porcine coronary arteries.
2003 Nov 14
Studies with cytotoxic agents suggest that apoptosis is not a major determinant of clonogenic death in neuroblastoma cells.
2003 Oct
Anti-leukemia effect of perillyl alcohol in Bcr/Abl-transformed cells indirectly inhibits signaling through Mek in a Ras- and Raf-independent fashion.
2003 Oct 1
Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro.
2003 Oct 17
Gateways to clinical trials.
2003 Sep
Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells.
2003 Sep 15
Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test.
2004 Apr 20
Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.
2004 Feb
Transformation of terpenes using a Picea abies suspension culture.
2004 Jan 22
Development of a perillyl alcohol topical cream formulation.
2004 Jan 28
Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention.
2004 Jul
BAK overexpression mediates p53-independent apoptosis inducing effects on human gastric cancer cells.
2004 Jul 12
Gateways to clinical trials.
2004 Mar
A pilot surrogate end point biomarker trial of perillyl alcohol in breast neoplasia.
2004 Nov 15
Inherent growth advantage of (pre)malignant hepatocytes associated with nuclear translocation of pro-transforming growth factor alpha.
2004 Nov 29
Repellency of essential oils of some Kenyan plants against Anopheles gambiae.
2004 Oct
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
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
Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes.
2005 Feb 1
Cancer preventive role of selected dietary factors.
2005 Jan-Mar
Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto.
2005 Mar
Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells.
2005 May
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
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.
2006 Aug
Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review.
2006 Dec
Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells.
2006 Jun 1
Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells.
2007 Nov 18
Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer.
2008
Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis.
2008 Jul
A pilot study of perillyl alcohol in pancreatic cancer.
2008 Jun 15
Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells.
2008 Mar-Apr
GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data.
2009 Feb 24
Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin.
2010 Jan
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:32:34 UTC 2021
Edited
by admin
on Sat Jun 26 07:32:34 UTC 2021
Record UNII
3UL4QIY642
Record Status Validated (UNII)
Record Version
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Name Type Language
PERILLA ALCOHOL
Common Name English
NEO-100
Brand 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
Brand Name 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 Sat Jun 26 07:32:34 UTC 2021 , Edited by admin on Sat Jun 26 07:32:34 UTC 2021
Code System Code Type Description
PUBCHEM
369312
Created by admin on Sat Jun 26 07:32:34 UTC 2021 , Edited by admin on Sat Jun 26 07:32:34 UTC 2021
PRIMARY
CAS
18457-55-1
Created by admin on Sat Jun 26 07:32:34 UTC 2021 , Edited by admin on Sat Jun 26 07:32:34 UTC 2021
PRIMARY
FDA UNII
3UL4QIY642
Created by admin on Sat Jun 26 07:32:34 UTC 2021 , Edited by admin on Sat Jun 26 07:32:34 UTC 2021
PRIMARY
Related Record Type Details
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