MedKoo Cat#: 412215 | Name: Cacalol

Description:

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

Cacalol is a sesquiterpene contained in Cacalia delphiniifolia Sleb et Zucc.

Chemical Structure

Cacalol
Cacalol
CAS#24393-79-1

Theoretical Analysis

MedKoo Cat#: 412215

Name: Cacalol

CAS#: 24393-79-1

Chemical Formula: C15H18O2

Exact Mass: 230.1307

Molecular Weight: 230.31

Elemental Analysis: C, 78.23; H, 7.88; O, 13.89

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Cacalol
IUPAC/Chemical Name
Naphtho(2,3-b)furan-9-ol, 5,6,7,8-tetrahydro-3,4,5-trimethyl-, (S)-
InChi Key
OUFUBABGIIEJNV-QMMMGPOBSA-N
InChi Code
InChI=1S/C15H18O2/c1-8-5-4-6-11-12(8)10(3)13-9(2)7-17-15(13)14(11)16/h7-8,16H,4-6H2,1-3H3/t8-/m0/s1
SMILES Code
OC1=C2OC=C(C)C2=C(C)C3=C1CCC[C@@H]3C
Appearance
Solid powder
Purity
>98% (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
Shelf Life
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 230.31 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
1: Mora-Ramiro B, Jiménez-Estrada M, Zentella-Dehesa A, Ventura-Gallegos JL, Gomez-Quiroz LE, Rosiles-Alanis W, Alarcón-Aguilar FJ, Almanza-Pérez JC. Cacalol Acetate, a Sesquiterpene from Psacalium decompositum, Exerts an Anti- inflammatory Effect through LPS/NF-KB Signaling in Raw 264.7 Macrophages. J Nat Prod. 2020 Aug 28;83(8):2447-2455. doi: 10.1021/acs.jnatprod.0c00300. Epub 2020 Jul 16. PMID: 32672964. 2: Mo H, Jeter R, Bachmann A, Yount ST, Shen CL, Yeganehjoo H. The Potential of Isoprenoids in Adjuvant Cancer Therapy to Reduce Adverse Effects of Statins. Front Pharmacol. 2019 Jan 4;9:1515. doi: 10.3389/fphar.2018.01515. PMID: 30662405; PMCID: PMC6328495. 3: Castillo-Arellano JI, Gómez-Verjan JC, Rojano-Vilchis NA, Mendoza-Cruz M, Jiménez-Estrada M, López-Valdés HE, Martínez-Coria H, Gutiérrez-Juárez R, González-Espinosa C, Reyes-Chilpa R, Arrieta-Cruz I. Chemoinformatic Analysis of Selected Cacalolides from Psacalium decompositum (A. Gray) H. Rob. & Brettell and Psacalium peltatum (Kunth) Cass. and Their Effects on FcεRI- Dependent Degranulation in Mast Cells. Molecules. 2018 Dec 19;23(12):3367. doi: 10.3390/molecules23123367. PMID: 30572603; PMCID: PMC6321304. 4: Kuroda C, Kobayashi R, Nagata A, Nakadozono Y, Itoh T, Okamoto Y, Tori M, Hanai R, Gong X. Terpenoids and Phenylpropanoids in Ligularia duciformis, L. kongkalingensis, L. nelumbifolia, and L. limprichtii. Molecules. 2017 Nov 25;22(12):2062. doi: 10.3390/molecules22122062. PMID: 29186833; PMCID: PMC6149998. 5: Tori M. Terpenoid Composition and Base Sequences of Ligularia virgaurea (Asteraceae) Grown in the Hengduan Mountain Area in China and a Comment on Drawing Structures. Chem Pharm Bull (Tokyo). 2016;64(3):193-206. doi: 10.1248/cpb.c15-00878. PMID: 26936046. 6: Garduño-Ramírez ML, Clares B, Domínguez-Villegas V, Peraire C, Ruiz MA, García ML, Calpena AC. Skin permeation of cacalol, cacalone and 6-epi-cacalone sesquiterpenes from a nanoemulsion. Nat Prod Commun. 2012 Jul;7(7):821-3. PMID: 22908555. 7: Liu W, Furuta E, Shindo K, Watabe M, Xing F, Pandey PR, Okuda H, Pai SK, Murphy LL, Cao D, Mo YY, Kobayashi A, Iiizumi M, Fukuda K, Xia B, Watabe K. Cacalol, a natural sesquiterpene, induces apoptosis in breast cancer cells by modulating Akt-SREBP-FAS signaling pathway. Breast Cancer Res Treat. 2011 Jul;128(1):57-68. doi: 10.1007/s10549-010-1076-8. Epub 2010 Jul 28. PMID: 20665104. 8: Campos MG, Oropeza M, Torres-Sosa C, Jiménez-Estrada M, Reyes-Chilpa R. Sesquiterpenoids from antidiabetic Psacalium decompositum block ATP sensitive potassium channels. J Ethnopharmacol. 2009 Jun 25;123(3):489-93. doi: 10.1016/j.jep.2009.03.003. Epub 2009 Mar 20. PMID: 19501281. 9: Kedrowski BL, Hoppe RW. A concise synthesis of (+/-)-cacalol. J Org Chem. 2008 Jul 4;73(13):5177-9. doi: 10.1021/jo800324c. Epub 2008 May 29. PMID: 18507439. 10: Burgueño-Tapia E, González-Coloma A, Martín-Benito D, Joseph-Nathan P. Antifeedant and phytotoxic activity of cacalolides and eremophilanolides. Z Naturforsch C J Biosci. 2007 May-Jun;62(5-6):362-6. doi: 10.1515/znc-2007-5-608. PMID: 17708441. 11: Torihata A, Hanai R, Gong X, Shen Y, Kuroda C. Chemical and genetic differentiation of Ligularia tsangchanensis in Yunnan and Sichuan provinces of China. Chem Biodivers. 2007 Mar;4(3):500-7. doi: 10.1002/cbdv.200790042. PMID: 17372952. 12: Arciniegas A, Pérez-Castorena AL, Villaseñor JL, Romo de Vivar A. Cacalol derivatives from Roldana angulifolia. J Nat Prod. 2006 Dec;69(12):1826-9. doi: 10.1021/np0604073. PMID: 17190472. 13: Wu QX, We QY, Shi YP. Sesquiterpenes with various carbon skeletons from Ligularia virgaurea spp. oligocephala. Pharmazie. 2006 Mar;61(3):241-3. PMID: 16599268. 14: Jimenez-Estrada M, Chilpa RR, Apan TR, Lledias F, Hansberg W, Arrieta D, Aguilar FJ. Anti-inflammatory activity of cacalol and cacalone sesquiterpenes isolated from Psacalium decompositum. J Ethnopharmacol. 2006 Apr 21;105(1-2):34-8. doi: 10.1016/j.jep.2005.09.039. Epub 2005 Nov 22. PMID: 16307855. 15: Shindo K, Kimura M, Iga M. Potent antioxidative activity of cacalol, a sesquiterpene contained in Cacalia delphiniifolia Sleb et Zucc. Biosci Biotechnol Biochem. 2004 Jun;68(6):1393-4. doi: 10.1271/bbb.68.1393. PMID: 15215613. 16: Garofalo AW, Litvak J, Wang L, Dubenko LG, Cooper R, Bierer DE. Total Synthesis of Cacalol. J Org Chem. 1999 Apr 30;64(9):3369-3372. doi: 10.1021/jo9822838. PMID: 11674448. 17: Garduño-Ramírez ML, Trejo A, Navarro V, Bye R, Linares E, Delgado G. New modified eremophilanes from the roots of Psacalium radulifolium. J Nat Prod. 2001 Apr;64(4):432-5. doi: 10.1021/np000385z. PMID: 11325222. 18: Alarcon-Aguilar FJ, Jimenez-Estrada M, Reyes-Chilpa R, Gonzalez-Paredes B, Contreras CC, Roman-Ramos R. Hypoglycemic activity of root water decoction, sesquiterpenoids, and one polysaccharide fraction from Psacalium decompositum in mice. J Ethnopharmacol. 2000 Mar;69(3):207-15. doi: 10.1016/s0378-8741(99)00039-2. PMID: 10722202. 19: Inman WD, Luo J, Jolad SD, King SR, Cooper R. Antihyperglycemic sesquiterpenes from Psacalium decompositum. J Nat Prod. 1999 Aug;62(8):1088-92. doi: 10.1021/np990023v. PMID: 10479309. 20: Chen HM, Wang YY, Mao JM, Cai MS, Jia ZJ. Syntheses and pharmacological activities of the derivatives of furanosesquiterpenes from Ligularia virgaurea. Planta Med. 1997 Aug;63(4):299-302. doi: 10.1055/s-2006-957686. PMID: 17252389.