Bacteriochlorophyll a | CAS#17499-98-8

MedKoo Cat#: 330053 | Name: Bacteriochlorophyll a

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Description:

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

Bacteriochlorophyll a is a Bacteriochlorophyll from Rhodopseudomonas sphaeroides. The compounds of this class strongly absorb light at lambda=770-850 nm. This unique property opens new therapeutic opportunities due to deeper tissue penetration of light, thereby increasing the photodamage for tumor eradication.

Chemical Structure

Bacteriochlorophyll a

CAS#17499-98-8

Theoretical Analysis

MedKoo Cat#: 330053

Name: Bacteriochlorophyll a

CAS#: 17499-98-8

Chemical Formula: C55H74MgN4O6

Exact Mass: 910.5459

Molecular Weight: 911.52

Elemental Analysis: C, 72.47; H, 8.18; Mg, 2.67; N, 6.15; O, 10.53

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1mg	USD 550.00	2 Weeks

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Synonym

Bacteriochlorophyll a; Bacteriochlorophyll; C11242; C 11242; C-11242; Bacteriochlorophyll from Rhodopseudomonas sphaeroides;

IUPAC/Chemical Name

magnesium;methyl (3R,11R,12R,21S,22S)-16-acetyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-[3-oxo-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-23,25-diaza-7,24-diazanidahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1(23),2(6),5(26),8,10(25),13,15,17,19-nonaene-3-carboxylate

InChi Key

DSJXIQQMORJERS-AGGZHOMASA-M

InChi Code

InChI=1S/C55H75N4O6.Mg/c1-13-39-34(7)41-29-46-48(38(11)60)36(9)43(57-46)27-42-35(8)40(52(58-42)50-51(55(63)64-12)54(62)49-37(10)44(59-53(49)50)28-45(39)56-41)23-24-47(61)65-26-25-33(6)22-16-21-32(5)20-15-19-31(4)18-14-17-30(2)3;/h25,27-32,34-35,39-40,51H,13-24,26H2,1-12H3,(H-,56,57,58,59,60,62);/q-1;+2/p-1/b33-25+;/t31-,32-,34-,35+,39-,40+,51-;/m1./s1

SMILES Code

CC[C@@H]1[C@H](C2=CC3=C(C(=C([N-]3)C=C4[C@H]([C@@H](C(=N4)C5=C6C(=C(C(=CC1=N2)[N-]6)C)C(=O)[C@@H]5C(=O)OC)CCC(=O)OC/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C)C(=O)C)C.[Mg+2]

Appearance

Solid powder

Purity

>95% (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

Bacteriochlorophylls (BChl) are photosynthetic pigments that occur in various phototrophic bacteria. They were discovered by C. B. van Niel in 1932. They are related to chlorophylls, which are the primary pigments in plants, algae, and cyanobacteria. Organisms that contain bacteriochlorophyll conduct photosynthesis to sustain their energy requirements, but do not produce oxygen as a byproduct. They use wavelengths of light not absorbed by plants or Cyanobacteria. Replacement of Mg2+ with protons gives bacteriophaeophytin (BPh), the phaeophytin form. ---from https://en.wikipedia.org/wiki/Bacteriochlorophyll.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 911.52 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.

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

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Aquabacterium pictum sp. nov., the first aerobic bacteriochlorophyll a-containing fresh water bacterium in the genus Aquabacterium of the class Betaproteobacteria. Int J Syst Evol Microbiol. 2020 Jan;70(1):596-603. doi: 10.1099/ijsem.0.003798. PMID: 31622237. 4: Meneghin E, Pedron D, Collini E. Spectroscopy data for the time and frequency characterization of vibrational coherences in bacteriochlorophyll a. Data Brief. 2019 Mar 7;23:103707. doi: 10.1016/j.dib.2019.103707. PMID: 31372380; PMCID: PMC6660430. 5: Rätsep M, Linnanto JM, Freiberg A. Higher Order Vibronic Sidebands of Chlorophyll a and Bacteriochlorophyll a for Enhanced Excitation Energy Transfer and Light Harvesting. J Phys Chem B. 2019 Aug 22;123(33):7149-7156. doi: 10.1021/acs.jpcb.9b06843. Epub 2019 Aug 9. PMID: 31356081. 6: Anda A, Hansen T, De Vico L. Q y and Q x Absorption Bands for Bacteriochlorophyll a Molecules from LH2 and LH3. J Phys Chem A. 2019 Jun 27;123(25):5283-5292. doi: 10.1021/acs.jpca.9b02877. 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Coherences of Bacteriochlorophyll a Uncovered Using 3D-Electronic Spectroscopy. J Phys Chem Lett. 2018 Oct 18;9(20):6077-6081. doi: 10.1021/acs.jpclett.8b02217. Epub 2018 Oct 5. PMID: 30273488. 11: Saga Y, Hirota K, Matsui S, Asakawa H, Ishikita H, Saito K. Selective Removal of B800 Bacteriochlorophyll a from Light-Harvesting Complex 2 of the Purple Photosynthetic Bacterium Phaeospirillum molischianum. Biochemistry. 2018 May 29;57(21):3075-3083. doi: 10.1021/acs.biochem.8b00259. Epub 2018 May 17. PMID: 29771536. 12: Leiger K, Linnanto JM, Freiberg A. Vibronic Origin of the Qy Absorption Tail of Bacteriochlorophyll a Verified by Fluorescence Excitation Spectroscopy and Quantum Chemical Simulations. J Phys Chem Lett. 2017 Sep 7;8(17):4231-4235. doi: 10.1021/acs.jpclett.7b01704. Epub 2017 Aug 24. PMID: 28820595. 13: Saga Y, Hirota K, Asakawa H, Takao K, Fukuma T. 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Epub 2017 Feb 22. PMID: 28225270. 16: Kim CW, Rhee YM. Constructing an Interpolated Potential Energy Surface of a Large Molecule: A Case Study with Bacteriochlorophyll a Model in the Fenna- Matthews-Olson Complex. J Chem Theory Comput. 2016 Nov 8;12(11):5235-5246. doi: 10.1021/acs.jctc.6b00647. Epub 2016 Oct 28. PMID: 27760297. 17: Calvano CD, Ventura G, Trotta M, Bianco G, Cataldi TR, Palmisano F. Electron-Transfer Secondary Reaction Matrices for MALDI MS Analysis of Bacteriochlorophyll a in Rhodobacter sphaeroides and Its Zinc and Copper Analogue Pigments. J Am Soc Mass Spectrom. 2017 Jan;28(1):125-135. doi: 10.1007/s13361-016-1514-x. Epub 2016 Oct 11. PMID: 27730524. 18: Saga Y, Hirota K. Determination of the Molar Extinction Coefficients of the B800 and B850 Absorption Bands in Light-harvesting Complexes 2 Derived from Three Purple Photosynthetic Bacteria Rhodoblastus acidophilus, Rhodobacter sphaeroides, and Phaeospirillum molischianum by Extraction of Bacteriochlorophyll a. Anal Sci. 2016;32(7):801-4. doi: 10.2116/analsci.32.801. PMID: 27396664. 19: Lehours AC, Jeune AL, Aguer JP, Céréghino R, Corbara B, Kéraval B, Leroy C, Perrière F, Jeanthon C, Carrias JF. Unexpectedly high bacteriochlorophyll a concentrations in neotropical tank bromeliads. Environ Microbiol Rep. 2016 Oct;8(5):689-698. doi: 10.1111/1758-2229.12426. Epub 2016 Jul 12. PMID: 27264016. 20: Cardona T. Origin of Bacteriochlorophyll a and the Early Diversification of Photosynthesis. PLoS One. 2016 Mar 8;11(3):e0151250. doi: 10.1371/journal.pone.0151250. PMID: 26953697; PMCID: PMC4783071.