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MedKoo Cat#: 407322 | Name: Perillyl alcohol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Perillyl alcohol, or POH, is a naturally occurring monocyclic terpenes derived from the mevalonate pathway in plants. Perillyl alcohol can be found in the essential oils of various botanicals, such as lavender, lemongrass, sage, and peppermint. It has a number of manufacturing, household, and medical applications. For example, perillyl alcohol may be used as an ingredient in cleaning products and cosmetics, and it has shown promise for inhalation therapy of patients with brain cancer.

Chemical Structure

Perillyl alcohol
Perillyl alcohol
CAS#18457-55-1

Theoretical Analysis

MedKoo Cat#: 407322

Name: Perillyl alcohol

CAS#: 18457-55-1

Chemical Formula: C10H16O

Exact Mass: 152.1201

Molecular Weight: 152.24

Elemental Analysis: C, 78.90; H, 10.59; O, 10.51

Price and Availability

Size Price Availability Quantity
5g USD 250.00
10g USD 450.00
20g USD 650.00
50g USD 950.00
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Related CAS #
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Synonym
Perillyl alcohol; Perilla alcohol; Perycorolle; POH; perillol; perillic alcohol;
IUPAC/Chemical Name
(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol
InChi Key
NDTYTMIUWGWIMO-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
SMILES Code
C=C(C1CC=C(CO)CC1)C
Appearance
Colorless to Pale Yellow liquid
Purity
>96% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
In vitro studies show that POH has antiangiogenesis and anticancer effects. Early animal studies also suggest tumor inhibition and regression. In human studies, oral POH did not benefit patients with prostate, ovarian, or breast cancers. Another study attempting to achieve higher daily oral doses or better long-term tolerability in a variety of malignant tumors found no significant advantages with interrupted administration over continuous dosing schedules. Topical POH also did not show chemopreventive effects in subjects with skin damage. These delivery methods were consequently abandoned due to either dose-limiting side effects and/or lack of efficacy. More recent preliminary studies found intranasal POH 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. Confirmatory studies are needed. copied from https://www.mskcc.org/cancer-care/integrative-medicine/herbs/perillyl-alcohol
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#S20G01M21
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
(S)-(−)-Perillyl alcohol is a monoterpene found in lavender, inhibits farnesylation of Ras, upregulates the mannose-6-phosphate receptor and induces apoptosis. Anti-cancer activity.
In vitro activity:
In this study, the effects of perillyl alcohol (POH) and its analog, perillaldehyde (PALD), on human carcinoma cell lines (BroTo and A549) cultured in vitro were investigated using proliferation assays (MTT and colony formation) and DNA content analysis by flow cytometry. POH and PALD elicited dose- and time-dependent inhibition of proliferation in both cell lines. Concentrations of POH and PALD that inhibited cell proliferation by 50% (IC50) in 24 hr were 1 and 3 mM, respectively. DNA content analysis revealed that 1 mM of either POH or PALD caused cell cycle arrest in the G1 phase in both cell lines while POH alone caused increased hypodiploid and annexin V-positive populations in both BroTo and A549 cells. POH induced apoptosis and was more effective than PALD at inhibiting the proliferation of BroTo and A549 cells cultured in vitro. Reference: Life Sci. 2003 Oct 17;73(22):2831-40. https://pubmed.ncbi.nlm.nih.gov/14511768/
In vivo activity:
The purpose of the current research was to evaluate the effect of perillyl alcohol (PA) on oxidative stress and inflammation parameters in rats with allergic asthma. PA (perillyl alcohol) and Dexa (dexamethasone) decreased the pathological alterations and the expression levels of inflammatory factors (cytokines, GATA3, and NF-κB) in the lung tissue and BALF of asthmatic rats. PA restored GPx, SOD, and TAC levels and reduced ROS, MDA, nitrite, and total protein in the lung and BALF. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 28. https://pubmed.ncbi.nlm.nih.gov/36707429/
Solvent mg/mL mM
Solubility
DMSO 250.0 1,642.18
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 152.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yuri T, Danbara N, Tsujita-Kyutoku M, Kiyozuka Y, Senzaki H, Shikata N, Kanzaki H, Tsubura A. Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo. Breast Cancer Res Treat. 2004 Apr;84(3):251-60. doi: 10.1023/B:BREA.0000019966.97011.4d. PMID: 15026623. 2. Elegbede JA, Flores R, Wang RC. Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro. Life Sci. 2003 Oct 17;73(22):2831-40. doi: 10.1016/s0024-3205(03)00701-x. PMID: 14511768. 3. Bejeshk MA, Beik A, Aminizadeh AH, Salimi F, Bagheri F, Sahebazzamani M, Najafipour H, Rajizadeh MA. Perillyl alcohol (PA) mitigates inflammatory, oxidative, and histopathological consequences of allergic asthma in rats. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 28. doi: 10.1007/s00210-023-02398-5. Epub ahead of print. PMID: 36707429. 4. Puppala ER, Aochenlar SL, Shantanu PA, Ahmed S, Jannu AK, Jala A, Yalamarthi SS, Borkar RM, Tripathi DM, Naidu VGM. Perillyl alcohol attenuates chronic restraint stress aggravated dextran sulfate sodium-induced ulcerative colitis by modulating TLR4/NF-κB and JAK2/STAT3 signaling pathways. Phytomedicine. 2022 Nov;106:154415. doi: 10.1016/j.phymed.2022.154415. Epub 2022 Aug 22. PMID: 36070663.
In vitro protocol:
1. Yuri T, Danbara N, Tsujita-Kyutoku M, Kiyozuka Y, Senzaki H, Shikata N, Kanzaki H, Tsubura A. Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo. Breast Cancer Res Treat. 2004 Apr;84(3):251-60. doi: 10.1023/B:BREA.0000019966.97011.4d. PMID: 15026623. 2. Elegbede JA, Flores R, Wang RC. Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro. Life Sci. 2003 Oct 17;73(22):2831-40. doi: 10.1016/s0024-3205(03)00701-x. PMID: 14511768.
In vivo protocol:
1. Bejeshk MA, Beik A, Aminizadeh AH, Salimi F, Bagheri F, Sahebazzamani M, Najafipour H, Rajizadeh MA. Perillyl alcohol (PA) mitigates inflammatory, oxidative, and histopathological consequences of allergic asthma in rats. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 28. doi: 10.1007/s00210-023-02398-5. Epub ahead of print. PMID: 36707429. 2. Puppala ER, Aochenlar SL, Shantanu PA, Ahmed S, Jannu AK, Jala A, Yalamarthi SS, Borkar RM, Tripathi DM, Naidu VGM. Perillyl alcohol attenuates chronic restraint stress aggravated dextran sulfate sodium-induced ulcerative colitis by modulating TLR4/NF-κB and JAK2/STAT3 signaling pathways. Phytomedicine. 2022 Nov;106:154415. doi: 10.1016/j.phymed.2022.154415. Epub 2022 Aug 22. PMID: 36070663.
1: Song X, Xie L, Wang X, Zeng Q, Chen TC, Wang W, Song X. Temozolomide-perillyl alcohol conjugate induced reactive oxygen species accumulation contributes to its cytotoxicity against non-small cell lung cancer. Sci Rep. 2016 Mar 7;6:22762. doi: 10.1038/srep22762. PubMed PMID: 26949038; PubMed Central PMCID: PMC4780103. 2: Paduch R, Trytek M, Król SK, Kud J, Frant M, Kandefer-Szerszeń M, Fiedurek J. Biological activity of terpene compounds produced by biotechnological methods. Pharm Biol. 2016 Jun;54(6):1096-107. doi: 10.3109/13880209.2015.1103753. Epub 2016 Jan 25. PubMed PMID: 26808720. 3: Faridi U, Dhawan SS, Pal S, Gupta S, Shukla AK, Darokar MP, Sharma A, Shasany AK. Repurposing L-Menthol for Systems Medicine and Cancer Therapeutics? L-Menthol Induces Apoptosis through Caspase 10 and by Suppressing HSP90. OMICS. 2016 Jan;20(1):53-64. doi: 10.1089/omi.2015.0118. PubMed PMID: 26760959; PubMed Central PMCID: PMC4739352. 4: Jhaveri N, Agasse F, Armstrong D, Peng L, Commins D, Wang W, Rosenstein-Sisson R, Vaikari VP, Santiago SV, Santos T, Chen L, Schönthal AH, Chen TC, Hofman FM. A novel drug conjugate, NEO212, targeting proneural and mesenchymal subtypes of patient-derived glioma cancer stem cells. Cancer Lett. 2016 Feb 28;371(2):240-50. doi: 10.1016/j.canlet.2015.11.040. Epub 2015 Dec 9. PubMed PMID: 26683773. 5: Xie L, Song X, Guo W, Wang X, Wei L, Li Y, Lv L, Wang W, Chen TC, Song X. Therapeutic effect of TMZ-POH on human nasopharyngeal carcinoma depends on reactive oxygen species accumulation. Oncotarget. 2016 Jan 12;7(2):1651-62. doi: 10.18632/oncotarget.6410. PubMed PMID: 26625208. 6: Ma Y, Bian J, Zhang F. Inhibition of perillyl alcohol on cell invasion and migration depends on the Notch signaling pathway in hepatoma cells. Mol Cell Biochem. 2016 Jan;411(1-2):307-15. doi: 10.1007/s11010-015-2593-x. Epub 2015 Oct 17. PubMed PMID: 26475687. 7: Andrade LN, Lima TC, Amaral RG, Pessoa Cdo Ó, Filho MO, Soares BM, Nascimento LG, Carvalho AA, de Sousa DP. Evaluation of the cytotoxicity of structurally correlated p-menthane derivatives. Molecules. 2015 Jul 21;20(7):13264-80. doi: 10.3390/molecules200713264. PubMed PMID: 26197313. 8: Chen TC, Fonseca CO, Schönthal AH. Preclinical development and clinical use of perillyl alcohol for chemoprevention and cancer therapy. Am J Cancer Res. 2015 Apr 15;5(5):1580-93. eCollection 2015. Review. PubMed PMID: 26175929; PubMed Central PMCID: PMC4497427. 9: Garcia DG, de Castro-Faria-Neto HC, da Silva CI, de Souza e Souza KF, Gonçalves-de-Albuquerque CF, Silva AR, de Amorim LM, Freire AS, Santelli RE, Diniz LP, Gomes FC, Faria MV, Burth P. Na/K-ATPase as a target for anticancer drugs: studies with perillyl alcohol. Mol Cancer. 2015 May 15;14:105. doi: 10.1186/s12943-015-0374-5. PubMed PMID: 25976744; PubMed Central PMCID: PMC4432499. 10: Chen TC, Cho HY, Wang W, Nguyen J, Jhaveri N, Rosenstein-Sisson R, Hofman FM, Schönthal AH. A novel temozolomide analog, NEO212, with enhanced activity against MGMT-positive melanoma in vitro and in vivo. Cancer Lett. 2015 Mar 28;358(2):144-51. doi: 10.1016/j.canlet.2014.12.021. Epub 2014 Dec 15. PubMed PMID: 25524552. 11: Afshordel S, Kern B, Clasohm J, König H, Priester M, Weissenberger J, Kögel D, Eckert GP. Lovastatin and perillyl alcohol inhibit glioma cell invasion, migration, and proliferation--impact of Ras-/Rho-prenylation. Pharmacol Res. 2015 Jan;91:69-77. doi: 10.1016/j.phrs.2014.11.006. Epub 2014 Dec 8. PubMed PMID: 25497898. 12: Azimi H, Khakshur AA, Abdollahi M, Rahimi R. Potential New Pharmacological Agents Derived From Medicinal Plants for the Treatment of Pancreatic Cancer. Pancreas. 2015 Jan;44(1):11-5. doi: 10.1097/MPA.0000000000000175. PubMed PMID: 25493374. 13: Gupta S, Marko MG, Miller VA, Schaefer FT, Anthony JR, Porter JR. Novel production of terpenoids in Escherichia coli and activities against breast cancer cell lines. Appl Biochem Biotechnol. 2015 Mar;175(5):2319-31. doi: 10.1007/s12010-014-1382-4. Epub 2014 Dec 9. PubMed PMID: 25484192. 14: Cho HY, Wang W, Jhaveri N, Lee DJ, Sharma N, Dubeau L, Schönthal AH, Hofman FM, Chen TC. NEO212, temozolomide conjugated to perillyl alcohol, is a novel drug for effective treatment of a broad range of temozolomide-resistant gliomas. Mol Cancer Ther. 2014 Aug;13(8):2004-17. doi: 10.1158/1535-7163.MCT-13-0964. Epub 2014 Jul 3. PubMed PMID: 24994771. 15: Hui Z, Zhang M, Cong L, Xia M, Dong J. Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives. Molecules. 2014 May 22;19(5):6671-82. doi: 10.3390/molecules19056671. PubMed PMID: 24858099. 16: Chen TC, Cho HY, Wang W, Barath M, Sharma N, Hofman FM, Schönthal AH. A novel temozolomide-perillyl alcohol conjugate exhibits superior activity against breast cancer cells in vitro and intracranial triple-negative tumor growth in vivo. Mol Cancer Ther. 2014 May;13(5):1181-93. doi: 10.1158/1535-7163.MCT-13-0882. Epub 2014 Mar 12. PubMed PMID: 24623736. 17: Peterson A, Bansal A, Hofman F, Chen TC, Zada G. A systematic review of inhaled intranasal therapy for central nervous system neoplasms: an emerging therapeutic option. J Neurooncol. 2014 Feb;116(3):437-46. doi: 10.1007/s11060-013-1346-5. Epub 2014 Jan 8. Review. PubMed PMID: 24398618. 18: DA Fonseca CO, Teixeira RM, Silva JC, DE Saldanha DA Gama Fischer J, Meirelles OC, Landeiro JA, Quirico-Santos T. Long-term outcome in patients with recurrent malignant glioma treated with Perillyl alcohol inhalation. Anticancer Res. 2013 Dec;33(12):5625-31. PubMed PMID: 24324108. 19: D'Alincourt Salazar M, da Silva RF, Da Fonseca CO, Lagrota-Candido J, Quirico-Santos T. Intranasal administration of perillyl alcohol activates peripheral and bronchus-associated immune system in vivo. Arch Immunol Ther Exp (Warsz). 2014 Feb;62(1):59-66. doi: 10.1007/s00005-013-0262-x. Epub 2013 Nov 21. PubMed PMID: 24257817. 20: Sarkar S, Azab B, Quinn BA, Shen X, Dent P, Klibanov AL, Emdad L, Das SK, Sarkar D, Fisher PB. Chemoprevention gene therapy (CGT) of pancreatic cancer using perillyl alcohol and a novel chimeric serotype cancer terminator virus. Curr Mol Med. 2014 Jan;14(1):125-40. PubMed PMID: 24236457.

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