Sarcinaxanthin

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

MedKoo CAT#: 461802

CAS#: 11031-47-3

Description: Sarcinaxanthin is an antioxidative carotenoid.

Chemical Structure

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Sarcinaxanthin
CAS# 11031-47-3
Instruction

Theoretical Analysis

MedKoo Cat#: 461802
Name: Sarcinaxanthin
CAS#: 11031-47-3
Chemical Formula: C50H72O2
Exact Mass: 704.55
Molecular Weight: 705.120
Elemental Analysis: C, 85.17; H, 10.29; O, 4.54

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Sarcinaxanthin;

IUPAC/Chemical Name: (2E,2'E)-4,4'-((1R,1'R,3R,3'R)-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(2,2-dimethyl-4-methylenecyclohexane-3,1-diyl))bis(2-methylbut-2-en-1-ol)

InChi Key: XFXHBQLETDDGGF-XUYZKQIISA-N

InChi Code: InChI=1S/C50H72O2/c1-37(19-15-21-39(3)25-33-47-43(7)27-31-45(49(47,9)10)29-23-41(5)35-51)17-13-14-18-38(2)20-16-22-40(4)26-34-48-44(8)28-32-46(50(48,11)12)30-24-42(6)36-52/h13-26,33-34,45-48,51-52H,7-8,27-32,35-36H2,1-6,9-12H3/b14-13+,19-15+,20-16+,33-25+,34-26+,37-17+,38-18+,39-21+,40-22+,41-23+,42-24+/t45-,46-,47+,48+/m0/s1

SMILES Code: C/C(CO)=C\C[C@H]1CCC([C@H](C1(C)C)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(/C=C/C=C(/C=C/[C@@H]2C(CC[C@@H](C2(C)C)C/C=C(CO)\C)=C)C)C)=C

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 705.12 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:
In vitro protocol:
In vivo protocol:

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1: Osawa A, Ishii Y, Sasamura N, Morita M, Kasai H, Maoka T, Shindo K. Characterization and antioxidative activities of rare C(50) carotenoids-sarcinaxanthin, sarcinaxanthin monoglucoside, and sarcinaxanthin diglucoside-obtained from Micrococcus yunnanensis. J Oleo Sci. 2010;59(12):653-9. PubMed PMID: 21099143.

2: Netzer R, Stafsnes MH, Andreassen T, Goksøyr A, Bruheim P, Brautaset T. Biosynthetic pathway for γ-cyclic sarcinaxanthin in Micrococcus luteus: heterologous expression and evidence for diverse and multiple catalytic functions of C(50) carotenoid cyclases. J Bacteriol. 2010 Nov;192(21):5688-99. doi: 10.1128/JB.00724-10. Epub 2010 Aug 27. PubMed PMID: 20802040; PubMed Central PMCID: PMC2953688.

3: Swift IE, Milborrow BV. Stereochemistry of beta-, gamma-, and epsilon-ring formation in bacterial C50. J Biol Chem. 1981 Nov 25;256(22):11607-11. PubMed PMID: 7028738.

4: Heider SA, Peters-Wendisch P, Netzer R, Stafnes M, Brautaset T, Wendisch VF. Production and glucosylation of C50 and C 40 carotenoids by metabolically engineered Corynebacterium glutamicum. Appl Microbiol Biotechnol. 2014 Feb;98(3):1223-35. doi: 10.1007/s00253-013-5359-y. Epub 2013 Nov 24. PubMed PMID: 24270893.

5: Hertzberg S, Liaaen-Jensen S. Bacterial carotenoids. LIII. C50-carotenoids. 19. Absolute configuration of sarcinaxanthin and sarcinaxanthin mono-beta-d-glucoside. Isolation of sarcinaxanthin diglycoside. Acta Chem Scand B. 1977;B31(3):215-8. PubMed PMID: 855546.

6: Arpin N, Norgård S, Francis GW, Liaaen-Jensen S. Bacterial carotenoids. XLI. C50-carotenoids. 11. C45- and C50-carotenoids from Sarcina lutea--sarcinaxanthin. Acta Chem Scand. 1973;27(7):2321-34. PubMed PMID: 4778898.

7: Lale R, Berg L, Stüttgen F, Netzer R, Stafsnes M, Brautaset T, Vee Aune TE, Valla S. Continuous control of the flow in biochemical pathways through 5' untranslated region sequence modifications in mRNA expressed from the broad-host-range promoter Pm. Appl Environ Microbiol. 2011 Apr;77(8):2648-55. doi: 10.1128/AEM.02091-10. Epub 2011 Feb 18. PubMed PMID: 21335387; PubMed Central PMCID: PMC3126357.

8: Liaaen-Jensen S, Weeks OB, Strang RH, Thirkell D. Identity of the C-50-carotenoid dehydrogenans-P439 and sarcinaxanthin. Nature. 1967 Apr 22;214(5086):379-80. PubMed PMID: 6032832.

9: Hoffmann J, Bóna-Lovász J, Beuttler H, Altenbuchner J. In vivo and in vitro studies on the carotenoid cleavage oxygenases from Sphingopyxis alaskensis RB2256 and Plesiocystis pacifica SIR-1 revealed their substrate specificities and non-retinal-forming cleavage activities. FEBS J. 2012 Oct;279(20):3911-24. doi: 10.1111/j.1742-4658.2012.08751.x. Epub 2012 Sep 11. PubMed PMID: 22901074.

10: Weeks OB, Montes AR, Andrewes AG. Structure of the principal carotenoid pigment of Cellulomonas biazotea. J Bacteriol. 1980 Mar;141(3):1272-8. PubMed PMID: 6245065; PubMed Central PMCID: PMC293823.

11: Stafsnes MH, Josefsen KD, Kildahl-Andersen G, Valla S, Ellingsen TE, Bruheim P. Isolation and characterization of marine pigmented bacteria from Norwegian coastal waters and screening for carotenoids with UVA-blue light absorbing properties. J Microbiol. 2010 Feb;48(1):16-23. doi: 10.1007/s12275-009-0118-6. Epub 2010 Mar 11. PubMed PMID: 20221724.

12: Henke NA, Heider SAE, Hannibal S, Wendisch VF, Peters-Wendisch P. Isoprenoid Pyrophosphate-Dependent Transcriptional Regulation of Carotenogenesis in Corynebacterium glutamicum. Front Microbiol. 2017 Apr 24;8:633. doi: 10.3389/fmicb.2017.00633. eCollection 2017. PubMed PMID: 28484430; PubMed Central PMCID: PMC5401885.

13: Taniguchi H, Henke NA, Heider SAE, Wendisch VF. Overexpression of the primary sigma factor gene sigA improved carotenoid production by Corynebacterium glutamicum: Application to production of β-carotene and the non-native linear C50 carotenoid bisanhydrobacterioruberin. Metab Eng Commun. 2017 Jan 13;4:1-11. doi: 10.1016/j.meteno.2017.01.001. eCollection 2017 Jun. PubMed PMID: 29142827; PubMed Central PMCID: PMC5678898.