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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
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.
2000 Jan-Feb
Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model.
2002 Dec
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
Effects of perillyl alcohol on melanoma in the TPras mouse model.
2002 Jun
Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention.
2002 Nov-Dec
Phase I trial of perillyl alcohol administered four times daily continuously.
2003 Nov
Gateways to clinical trials.
2003 Sep
Perillyl alcohol as a radio-/chemosensitizer in malignant glioma.
2003 Sep 19
BAK overexpression mediates p53-independent apoptosis inducing effects on human gastric cancer cells.
2004 Jul 12
Perillyl alcohol is an angiogenesis inhibitor.
2004 Nov
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
Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells.
2005 May
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
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.
2006 Aug
Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells.
2006 May 18
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 Mar
Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol.
2008
Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer.
2008
A pilot study of perillyl alcohol in pancreatic cancer.
2008 Jun 15
Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma.
2008 May 19
Fragrance material review on p-mentha-1,8-dien-7-ol.
2008 Nov
Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas.
2008 Sep
Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol.
2009 Dec
Statin-induced muscle damage and atrogin-1 induction is the result of a geranylgeranylation defect.
2009 Sep
Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin.
2010 Jan
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:20:34 GMT 2023
Edited
by admin
on Sat Dec 16 08:20:34 GMT 2023
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 Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
Code System Code Type Description
PUBCHEM
369312
Created by admin on Sat Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
PRIMARY
CHEBI
15420
Created by admin on Sat Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
PRIMARY
CAS
18457-55-1
Created by admin on Sat Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
PRIMARY
FDA UNII
3UL4QIY642
Created by admin on Sat Dec 16 08:20:34 GMT 2023 , Edited by admin on Sat Dec 16 08:20:34 GMT 2023
PRIMARY
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