MedKoo Cat#: 584018 | Name: Sugiol

Description:

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

Sugiol is a diterpene with anti-inflammatory activity from Calocedrus formosana bark.

Chemical Structure

Sugiol
Sugiol
CAS#511-05-7

Theoretical Analysis

MedKoo Cat#: 584018

Name: Sugiol

CAS#: 511-05-7

Chemical Formula: C20H28O2

Exact Mass: 300.2089

Molecular Weight: 300.44

Elemental Analysis: C, 79.96; H, 9.39; O, 10.65

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.
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Related CAS #
No Data
Synonym
Sugiol
IUPAC/Chemical Name
9(1H)-Phenanthrenone, 2,3,4,4a,10,10a-hexahydro-6-hydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-, (4aS-trans)- (9CI)
InChi Key
IPEHJNRNYPOFII-AZUAARDMSA-N
InChi Code
InChI=1S/C20H28O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,18,21H,6-8,11H2,1-5H3/t18-,20+/m0/s1
SMILES Code
O=C1C2=C(C=C(O)C(C(C)C)=C2)[C@@]3(C)CCCC(C)(C)[C@]3([H])C1
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 300.44 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: Hao C, Zhang X, Zhang H, Shang H, Bao J, Wang H, Li Z. Sugiol (127horbar;hydroxyabieta-8,11,13-trien-7-one) targets human pancreatic carcinoma cells (Mia-PaCa2) by inducing apoptosis, G2/M cell cycle arrest, ROS production and inhibition of cancer cell migration. J BUON. 2018 Jan-Feb;23(1):205-210. PubMed PMID: 29552785. 2: Jung SN, Shin DS, Kim HN, Jeon YJ, Yun J, Lee YJ, Kang JS, Han DC, Kwon BM. Sugiol inhibits STAT3 activity via regulation of transketolase and ROS-mediated ERK activation in DU145 prostate carcinoma cells. Biochem Pharmacol. 2015 Sep 1;97(1):38-50. doi: 10.1016/j.bcp.2015.06.033. Epub 2015 Jul 23. PubMed PMID: 26212545. 3: Bajpai VK, Kim NH, Kim K, Kang SC. Antiviral potential of a diterpenoid compound sugiol from Metasequoia glyptostroboides. Pak J Pharm Sci. 2016 May;29(3 Suppl):1077-80. PubMed PMID: 27383486. 4: Chao KP, Hua KF, Hsu HY, Su YC, Chang ST. Anti-inflammatory activity of sugiol, a diterpene isolated from Calocedrus formosana bark. Planta Med. 2005 Apr;71(4):300-5. PubMed PMID: 15856404. 5: Bajpai VK, Sharma A, Kang SC, Baek KH. Antioxidant, lipid peroxidation inhibition and free radical scavenging efficacy of a diterpenoid compound sugiol isolated from Metasequoia glyptostroboides. Asian Pac J Trop Med. 2014 Jan;7(1):9-15. doi: 10.1016/S1995-7645(13)60183-2. PubMed PMID: 24418075. 6: Scariot DB, Volpato H, Fernandes NS, Soares EFP, Ueda-Nakamura T, Dias-Filho BP, Din ZU, Rodrigues-Filho E, Rubira AF, Borges O, Sousa MDC, Nakamura CV. Activity and Cell-Death Pathway in Leishmania infantum Induced by Sugiol: Vectorization Using Yeast Cell Wall Particles Obtained From Saccharomyces cerevisiae. Front Cell Infect Microbiol. 2019 Jun 14;9:208. doi: 10.3389/fcimb.2019.00208. eCollection 2019. PubMed PMID: 31259161; PubMed Central PMCID: PMC6587907. 7: Córdova I, León LG, León F, San Andrés L, Luis JG, Padrón JM. Synthesis and antiproliferative activity of novel sugiol beta-amino alcohol analogs. Eur J Med Chem. 2006 Nov;41(11):1327-32. Epub 2006 Jul 7. PubMed PMID: 16828933. 8: Chen XJ, Ni L, Bao MF, Wang L, Cai XH. Abietane diterpenoids from Cephalotaxus lanceolata. Nat Prod Res. 2017 Nov;31(21):2473-2478. doi: 10.1080/14786419.2017.1314280. Epub 2017 Apr 12. PubMed PMID: 28399666. 9: Takei M, Umeyama A, Arihara S. Diterpenes inhibit IL-12 production by DC and enhance Th2 cells polarization. Biochem Biophys Res Commun. 2007 Apr 13;355(3):603-10. Epub 2007 Feb 6. PubMed PMID: 17316566. 10: Tsai CC, Chen CJ, Tseng HW, Hua KF, Tsai RY, Lai MH, Chao LK, Chen ST. Cytomic screening of immuno-modulating activity compounds from Calocedrus formosana. Comb Chem High Throughput Screen. 2008 Dec;11(10):834-42. PubMed PMID: 19075605. 11: Guo J, Ma X, Cai Y, Ma Y, Zhan Z, Zhou YJ, Liu W, Guan M, Yang J, Cui G, Kang L, Yang L, Shen Y, Tang J, Lin H, Ma X, Jin B, Liu Z, Peters RJ, Zhao ZK, Huang L. Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones. New Phytol. 2016 Apr;210(2):525-34. doi: 10.1111/nph.13790. Epub 2015 Dec 18. PubMed PMID: 26682704; PubMed Central PMCID: PMC4930649. 12: Chen YC, Li YC, You BJ, Chang WT, Chao LK, Lo LC, Wang SY, Huang GJ, Kuo YH. Diterpenoids with anti-inflammatory activity from the wood of Cunninghamia konishii. Molecules. 2013 Jan 4;18(1):682-9. doi: 10.3390/molecules18010682. PubMed PMID: 23292330; PubMed Central PMCID: PMC6269968. 13: Weng Y, Yu X, Li J, Dong Q, Li F, Cheng F, Zhang Y, Yao C, Zou Z, Zhou W, Tan G, Xu K. Abietane diterpenoids from Lycopodium complanatum. Fitoterapia. 2018 Jul;128:135-141. doi: 10.1016/j.fitote.2018.05.014. Epub 2018 May 21. PubMed PMID: 29772298. 14: Mothana RA, Khaled JM, El-Gamal AA, Noman OM, Kumar A, Alajmi MF, Al-Rehaily AJ, Al-Said MS. Comparative evaluation of cytotoxic, antimicrobial and antioxidant activities of the crude extracts of three Plectranthus species grown in Saudi Arabia. Saudi Pharm J. 2019 Feb;27(2):162-170. doi: 10.1016/j.jsps.2018.09.010. Epub 2018 Sep 25. PubMed PMID: 30766425; PubMed Central PMCID: PMC6362157. 15: Wang YR, Yu Y, Li SM, Liu W, Li W, Morris-Natschke SL, Goto M, Lee KH, Huang XF. Salvisertin A, a New Hexacyclic Triterpenoid, and Other Bioactive Terpenes from Salvia deserta Root. Chem Biodivers. 2018 Apr;15(4):e1800019. doi: 10.1002/cbdv.201800019. Epub 2018 Mar 25. PubMed PMID: 29451710; PubMed Central PMCID: PMC5912963. 16: Saijo H, Kofujita H, Takahashi K, Ashitani T. Antioxidant activity and mechanism of the abietane-type diterpene ferruginol. Nat Prod Res. 2015;29(18):1739-43. doi: 10.1080/14786419.2014.997233. Epub 2015 Jan 14. PubMed PMID: 25588148. 17: Khan MF, Dev K, Lahiri S, Dixit M, Trivedi R, Singh D, Maurya R. Osteogenic activity of natural diterpenoids isolated from Cupressus sempervirens fruits in calvarial derived osteoblast cells via differentiation and mineralization. Phytomedicine. 2014 Dec 15;21(14):1794-800. doi: 10.1016/j.phymed.2014.09.004. Epub 2014 Nov 6. PubMed PMID: 25481392. 18: Thommen C, Jana CK, Neuburger M, Gademann K. Syntheses of taiwaniaquinone F and taiwaniaquinol A via an unusual remote C-H functionalization. Org Lett. 2013 Mar 15;15(6):1390-3. doi: 10.1021/ol4003652. Epub 2013 Mar 5. PubMed PMID: 23461731. 19: Rajouani N, Ait Itto MY, Benharref A, Auhmani A, Daran JC. 6-Hydr-oxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexa-hydro-phenanthren-9( 1H)-one. Acta Crystallogr Sect E Struct Rep Online. 2008 Mar 29;64(Pt 4):o762. doi: 10.1107/S1600536808007769. PubMed PMID: 21202151; PubMed Central PMCID: PMC2960938. 20: Feng L, Mándi A, Tang C, Kurtán T, Tang S, Ke CQ, Shen N, Lin G, Yao S, Ye Y. A Pair of Enantiomeric Bis- seco-abietane Diterpenoids from Cryptomeria fortunei. J Nat Prod. 2018 Dec 28;81(12):2667-2672. doi: 10.1021/acs.jnatprod.8b00482. Epub 2018 Nov 28. PubMed PMID: 30485090.