PERILLYL ALCOHOL

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H16O
Molecular Weight	152.2334
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C)C1CCC(CO)=CC1

InChI

InChIKey=NDTYTMIUWGWIMO-UHFFFAOYSA-N

InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3

HIDE SMILES / InChI

Molecular Formula	C10H16O
Molecular Weight	152.2334
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02704858 | https://www.ncbi.nlm.nih.gov/pubmed/18726148 | https://www.ncbi.nlm.nih.gov/pubmed/26175929 | https://www.ncbi.nlm.nih.gov/pubmed/25976744

The monoterpene perillyl alcohol (POH) is a naturally occurring compound derived from citrus fruits, mint, and herbs. It exhibited chemotherapeutic potential against various malignant tumors in preclinical models and was being tested in clinical trials in patients with refractory advanced cancers. POH was formulated in soft gelatine capsules and orally administered to cancer patients several times a day on a continuous basis. However, such clinical trials in humans yielded disappointing results, also because of the large number of capsules that had to be swallowed caused hard-to-tolerate intestinal side effects, causing many patients to withdraw from treatment due to unrelenting nausea, fatigue, and vomiting. The clinical trials in Brazil have explored intranasal POH delivery as an alternative to circumvent the toxic limitations of oral administration. In these trials, patients with recurrent malignant gliomas were given comparatively small doses of POH via simple inhalation through the nose. Results from these studies showed, that this type of long-term, daily chemotherapy was well tolerated and effective. The precise mechanism of action is still undetermined, but it is known, that perillyl alcohol plays an important role in the process of hepatoma cell invasion and migration via decreasing the activity of Notch signaling pathway and increasing E-cadherin expression regulated by Snail. Another possible mechanism is included inhibition of Na/K-ATPase (NKA). The NKA α1 subunit is known to be superexpresses in glioblastoma cells (GBM) and POH acts in signaling cascades associated with NKA can control cell proliferation and/or cellular death.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Notch signaling pathway 3 Target ID: map04330 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475687	Inhibitor 8504
Sodium/potassium-transporting ATPase 34 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25976744	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 186 Sources: https://clinicaltrials.gov/ct2/show/NCT00003238	Primary	Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://clinicaltrials.gov/ct2/show/NCT00003219	Primary	Phase II 1147	Unknown Approved Use Unknown
Glioblastoma multiforme 30 Sources: https://clinicaltrials.gov/ct2/show/NCT02704858	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
604 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
48 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
26 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² 4 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
44 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
15 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
327 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² 4 times / day multiple, oral dose: 1600 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
442 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
600 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
225 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² 4 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
306 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
24 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
311 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
539 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² 4 times / day multiple, oral dose: 2000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
203 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
22 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
26 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² 4 times / day multiple, oral dose: 1600 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
66 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	200 mg/m² 4 times / day multiple, oral dose: 200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
22 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
2115 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
235 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² 4 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
208 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
57 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
766 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² 4 times / day multiple, oral dose: 1600 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1314 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2004 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
472 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² 4 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
871 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
72 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
813 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1248 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² 4 times / day multiple, oral dose: 2000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
663 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
89 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
77 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² 4 times / day multiple, oral dose: 1600 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
228 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	200 mg/m² 4 times / day multiple, oral dose: 200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
77 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	2000 mg/m² single, oral dose: 2000 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	PERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1600 mg/m² single, oral dose: 1600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15205914	1200 mg/m² single, oral dose: 1200 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	DIHYDROPERILLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY534436	https://www.001chemical.com/chem/18457-55-1
3B Scientific (Wuhan) Corp	3B3-081706	http://www.3bsc.com/index/pro_info.php?id=123246
AA Blocks	AA0038L5	http://www.aablocks.com/goods/Goods/detail?id=AA0038L5
Aaron Chemicals	AR0039CX	http://www.aaronchem.com/536-59-4
abcr GmbH	AB436265	http://www.abcr.com/shop/en/AB436265
Acadechem	ACDS-018567	http://www.acadechemical.com/product/93266
Acorn PharmaTech	ACN-056880	http://www.acornpharmatech.com/
AEchem Scientific Corp., USA	AE1-006168	http://www.aechemsc.com/info_products/AE1-006168.php
AHH Chemical co.,ltd	MR-1000200	http://www.ahhchemical.com/product/MR-1000200.html
AHH Chemical co.,ltd	MT-22467	http://www.ahhchemical.com/product/MT-22467.html
Alfa Chemistry	536-59-4	https://www.alfa-chemistry.com/dihydro-cuminyl-alcohol-cas-536-59-4-item-292481.htm
Ambeed	A114980	https://www.ambeed.com/products/536-59-4.html
Angel Pharmatech	AG111992	http://www.angelpharmatech.com/18457-55-1.html
Ark Pharm	AK117744	http://www.arkpharminc.com/products/536-59-4.html
Aurora Fine Chemicals LLC	K05.996.662	http://online.aurorafinechemicals.com/info?ID=K05.996.662
Aurum Pharmatech LLC	NE10108	http://www.Aurumpharmatech.com/Product/ProductDetails/NE10108
BioCrick	BCN3876	http://www.biocrick.com/Perillyl-alcohol-BCN3876.html
BLD Pharm	BD125009	http://www.bldpharm.com/products/536-59-4.html
BOC Sciences	18457-55-1	https://www.bocsci.com/perillyl-alcohol-cas-18457-55-1-item-350726.html
BOC Sciences	536-59-4	https://www.bocsci.com/dihydrocuminyl-alcohol-cas-536-59-4-item-93996.html
Chem Scene	CS-W019441	http://www.chemscene.com/536-59-4.html
ChemFaces	CFN93581	http://www.chemfaces.com/natural/Perillyl-alcohol-CFN93581.html
ChemMol	49414123	http://www.chemmol.com/chemmol/49414123.html
ChemMol	99101907	http://www.chemmol.com/chemmol/99101907.html
Chemspace	CSSB00000032513	https://chem-space.com/CSSB00000032513
Clearsynth	CS-E-00054	https://www.clearsynth.com/en/CSE00054.html
Combi-Blocks	QP-0933	http://www.combi-blocks.com/cgi-bin/find.cgi?QP-0933
CSNpharm	CSN10813	https://www.csnpharm.com/products/perillyl-alcohol.html
DC Chemicals	DC23000	http://www.dcchemicals.com/product_show-Perillyl_Alcohol.html
DC Chemicals	DC32529	http://www.dcchemicals.com//product_show-Perillyl_alcohol.html
DC Chemicals	DCZ-056	http://www.dcchemicals.com/product_show-Perillyl Alcohol.html
Debye Scientific	DB-065484	http://www.debyesci.com/cas_18457-55-1.html
Debye Scientific	DB-071728	http://www.debyesci.com/cas_536-59-4.html
eNovation Chemicals	D383389	http://www.enovationchem.com/productDetails.asp?productID=D383389
eNovation Chemicals	D660181	https://www.enovationchem.com/ProductDetails.asp?ProductID=D660181
eNovation Chemicals	D674709	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674709
Finetech	FT-0627990	http://www.finetechnology-ind.com/prod/detail/pub/536-59-4.html
Finetech	FT-0690515	http://www.finetechnology-ind.com/prod/detail/pub/18457-55-1.html
Hefei Hirisun Pharmatech Co., Ltd	HR012682	http://www.hirisunpharm.com/18457-55-1.html
iChemical	EBD44791	http://www.ichemical.com/chemicals/cas-536-59-4
Lab Network	LN00226580	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00226580
mcule	MCULE-1420218917	https://mcule.com/MCULE-1420218917/
MedChem Express	HY-N7000	https://www.medchemexpress.com/perillyl-alcohol.html
Molcore	MC534436	https://www.molcore.com/product/18457-55-1
MolPort	MolPort-003-665-516	https://www.molport.com/shop/molecule-link/MolPort-003-665-516
MuseChem	R072659	https://www.musechem.com/product/R072659.html
Nextpeptide	NP181479	http://www.nextpeptide.com/536-59-4.html
Parchem	20686	http://www.parchem.com/chemical-supplier-distributor/perilla-alcohol-010686.aspx
Selleck Chemicals	S3853	http://www.selleckchem.com/products/perillyl-alcohol.html
Sinfoo Biotech	S002910	http://www.sinfoobiotech.com/product/1006308
Smolecule	S539048	http://www.smolecule.com/products/s539048
Smolecule	S580323	https://www.smolecule.com/products/s580323
THE BioTek	bt-278920	https://www.thebiotek.com/product/inhibitors/bt-278920
THE BioTek	bt-298674	https://www.thebiotek.com/product/others/bt-298674
VladaChem	VL269097-10G	https://www.vladachem.com/product.php?products=536-59-4

PubMed

Title	Date	PubMed
Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin.	2010-01	19820395
Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol.	2009-12	19139816
Statin-induced muscle damage and atrogin-1 induction is the result of a geranylgeranylation defect.	2009-09	19406843
Perillyl alcohol attenuates Ras-ERK signaling to inhibit murine skin inflammation and tumorigenesis.	2009-05-15	19161993
Components of lemon essential oil attenuate dementia induced by scopolamine.	2009-04	19356307
GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data.	2009-02-24	19239707
[Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies].	2009-02	19388525
High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats.	2008-12-01	18849133
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	18845490
Fragrance material review on p-mentha-1,8-dien-7-ol.	2008-11	18640209
Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol.	2008-09-15	18768668
Gateways to clinical trials.	2008-09	18985183
Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas.	2008-09	18295834
PatternLab for proteomics: a tool for differential shotgun proteomics.	2008-07-21	18644148
Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.	2008-07-15	18556205
Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis.	2008-07	18645014
A pilot study of perillyl alcohol in pancreatic cancer.	2008-06-15	18498869
Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer.	2008-06	17885756
Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells.	2008-05-30	18507048
Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma.	2008-05-19	18489772
Ras pathway activation in gliomas: a strategic target for intranasal administration of perillyl alcohol.	2008-02-04	18726148
Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol.	2008	19227008
Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds.	2008	18561352
Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer.	2008	18444166
Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model.	2007-12	18227911
Rab-small GTPases are involved in fluvastatin and pravastatin-induced vacuolation in rat skeletal myofibers.	2007-12	17634390
Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells.	2007-11-18	17888568
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	17601486
Cloning of four genes involved in limonene hydroxylation from Enterobacter cowanii 6L.	2007-07	18051329
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	17138864
Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review.	2006-12	17145324
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.	2006-08	16926494
Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells.	2006-06-01	16307765
Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells.	2006-05-18	16029925
Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549.	2006	17024970
In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression.	2006	17008791
Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis.	2006	16965245
Apocynin derivatives interrupt intracellular signaling resulting in decreased migration in breast cancer cells.	2006	16883056
Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells.	2006	16439861
Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol.	2006	16427438
Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway.	2005-09-15	16166337
Regio- and stereoselective fungal oxyfunctionalisation of limonenes.	2005-07-27	16042348
Gateways to clinical trials.	2005-06	16082422
Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells.	2005-05	15809762
Effect of D-limonene on immune response in BALB/c mice with lymphoma.	2005-05	15778119
Cancer preventive role of selected dietary factors.	2005-04-05	15805687
An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation.	2005-03-09	15740902
Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto.	2005-03	15830848
Terpenoids as plant antioxidants.	2005	16492481
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	15959631

Patents

Sample Use Guides

In Vivo Use Guide

cancer: patients receive oral perillyl alcohol 4 times a day for 4 weeks. Patients continue treatment in the absence of severe toxicity and disease progression. Glioblastoma Multiforme: intranasal delivery of NEO100 (perillyl alcohol) four times a day, escalation up to four different doses to determine maximum tolerated dose. Doses of 96 mg qid, 144mg qid, 192mg qid, and 288 mg qid administered intranasally to patients with recurrent GBM for up to 6 months, disease progression or death.

Route of Administration: Other

In Vitro Use Guide

Perillyl alcohol (POH) inhibits cellular proliferation at the G1 phase of the cell cycle in vitro. 1.0 mM POH upregulates p15(INK4b) and p21(WAF1/Cip1), resulting in hypophosphorylation of the retinoblastoma (RB) protein and subsequent G1 arrest in human immortalized keratinocyte HaCaT cells. The induction of p15(INK4b) was mediated through its promoter, but that of p21(WAF1/Cip1) was not. The small interfering RNA (siRNA) of either p15(INK4b) or p21(WAF1/Cip1) significantly attenuated the increase in the G1 cell population caused by POH. The induction of p15(INK4b) and p21(WAF1/Cip1) and sub-sequent G1 arrest by POH was also observed in other cancer cell lines. These results suggest that the induction of p15(INK4b) as well as p21(WAF1/Cip1) is associated with the antiproliferative effect of POH.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:46 GMT 2025`
Record UNII	319R5C7293
Record Status	`Validated (UNII)`
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Name

Type

Language

P-MENTHA-1,8-DIEN-7-OL

Preferred Name

English

PERILLYL ALCOHOL

Official Name

English

NSC-641066

Code

English

1-CYCLOHEXENE-1-METHANOL, 4-(1-METHYLETHENYL)-

Systematic Name

English

PERILLOL

Common Name

English

(±)-1-CYCLOHEXENE-1-METHANOL, 4-(1-METHYLETHENYL)-

Systematic Name

English

HYDROCUMIN ALCOHOL

Common Name

English

FEMA NO. 2664

Code

English

DL-PERILLYL ALCOHOL

Common Name

English

P-MENTHA-1,8-DIEN-7-OL [FHFI]

Common Name

English

ISO-CARVEOL

Common Name

English

(±)-PERILLYL ALCOHOL

Common Name

English

DIHYDROCUMINYL ALCOHOL

Systematic Name

English

DIHYDROCUMINIC ALCOHOL

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 172.515