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Just Add Water
Going green gets organic solvents out of organic chemistry

Organic solvents are usually toxic, are created from the world’s petroleum reserves, and ultimately make up more than 70% of all chemical waste generated. Bruce Lipshutz, a chemistry professor at UC Santa Barbara, wants to get rid of them by replacing them with water… even seawater.

“Why not use the same technology, the same ‘trick’, we use to dissolve CoQ10 and many other nutraceuticals and pharmaceuticals in water?” asked Lipshutz. He theorized that if those bioactive compounds can be solubilized in water, then we should be able to do the same with organic reactants and their associated catalysts. That would then lead to the desired reaction products—in essence, organic chemistry in water.

Lipshutz has a strong history with CoQ10 in his lab. Initially, he retooled the chemistry to produce the supplement using synthesis rather than fermentation, the method that Japanese industry uses and which led to their world leadership position in CoQ10 production. China’s recent entry into the CoQ10 market, however, dramatically impacted pricing and availability of CoQ10.

When the supply of CoQ10 grew faster than demand, Lipshutz went back into the lab to study what else could be done with this life-sustaining compound. CoQ10 is readily available at Costco or drug stores, where you can buy it formulated into softgels that deliver the nutrient in various strengths. It’s marketed as helping to provide a boost in energy as well as a healthy heart. Lipshutz noted, however, that our bodies absorb only10-15 percent of the CoQ10 in the softgel form. How, he asked, could this become more available and bioefficient?

Never heard of CoQ10?

UC Santa Barbara chemist Bruce Lipshutz says you’re not alone if you haven’t. “If you don’t know anything about it,” Lipshutz said during a recent interview, “that’s not surprising—much of the public hasn’t heard of it.” He’s on a mission to correct what he views as a major oversight in human wellness, especially among baby-boomers: “Society needs not only to know about CoQ10, we need to think about it as a daily vitamin, and to take it .”

Like vitamin C, coenzyme Q10, also known as ubiquinone, is a compound that’s vital to our survival. It’s a coenzyme that our cells synthesize, albeit in 21 steps, and it’s in every one of our cells. This contrasts with a vitamin, such as vitamin C, which is not made by the body. Both CoQ10 and vitamin C are “compounds of evolution,” Lipshutz said. “Everybody accepts the importance of vitamin C. The reason the public doesn’t yet appreciate CoQ10 is that it’s had no celebrity champion—no Linus Pauling.” (Pauling, a Nobel Prize-winning chemist, was also a strong advocate for greater consumption of vitamin C.)

While the body produces its own CoQ10, that production decreases with age. “Nature gave us, through 2.5 billion years of evolution, a number of fundamental anti-aging, free-radical scavengers that helped us to survive, on average, to about 40 years of age, until modern medicine came along,” Lipshutz said. “Our ability to synthesize CoQ10 diminishes with aging beyond our prime, which is around 20.”

If one doesn’t get vitamin C, the consequences can be significant and ultimately hazardous to your health. “It’s essential for several cellular processes. For example, everyone knows about scurvy,” Lipshutz said. “You can last 30 days, maybe 60 days, without vitamin C as your cells deteriorate.”

On the other hand, CoQ10 – much of which is in the mitochondria of our cells – is essential for cellular respiration and for production of ATP (adenosine triphosphate), which facilitates energy generation within cells. “You couldn’t last 30 minutes without CoQ10,” he said. “Evolution teaches us that CoQ10 is as important as vitamin C. But who’s teaching this to our aging population? Nobody.”

Lipshutz went on to note, “While modern medicine has extended our longevity, some very common drugs can further reduce our naturally declining levels of CoQ10—for statin-based cholesterol-inhibiting drugs such as Lipitor and Zocor—also inhibit the body’s synthesis of CoQ10, by as much as 40-50%. This isn’t a side effect of statins, but a direct, inherent function of these drugs, since both cholesterol and CoQ10 are synthesized from the same precursors. That makes CoQ10 supplementation even more important for those taking statins; it’s the secret to getting rid of exercise intolerance and the muscle pain they can cause.”

Relevant links:
A good CoQ10 Overview

“The future isn’t about access to CoQ10,” he said. “It’s about getting it into water, so that we can deliver more of it and get more of it into the mitochondria of our cells.”

With CoQ10’s water insolubility, that was a significant challenge. Lipshutz found the answer in nanotechnology, which eventually became the tie-in to green chemistry.

“We aim to get organic solvents out of organic reactions,” he said. “And we’re already looking into next-generation possibilities. All of our green chemistry has come out of being able to put CoQ10 and other dietary supplements into water.”

“We do it with nano-micelle-forming technology,” Lipshutz said. He starts by putting a known, inexpensive molecule called PTS into water, in which it spontaneously forms nanoparticles averaging 25 nanometers (one nanometer is equal to one billionth of a meter) in diameter. These “designer” surfactants have a lipophilic portion tied to a hydrophilic portion through a linker. The lipophilic inner portion, which is actually vitamin E, self-associates because it doesn’t have any solubility (any energy-lowering interactions) with the surrounding water,” Lipshutz said. “But the external, or hydrophilic PEG portion, interacts well with water.”

The result is that when you add CoQ10, it says, ‘Where would I rather be?’ Since “like dissolves like,” the CoQ10 goes inside the micelles. Since they are only nanometers in diameter, the water in which CoQ10 is solubilized stays crystal clear. These solutions are also stable at room temperature.

“We can also take pharmaceuticals, like Taxol, an anti-tumor agent, and put them into just water or saline using this PTS,” he said. “The potential for broadening the range of drug delivery modalities for both existing and new drugs is tremendous.”

By taking advantage of this micellar technology, synthetic chemistry can also be done inside the micelles, where they function as nanoreactors. That translates into doing chemistry in pure water, and given the innate high concentrations of substrates within these micelles, reactions take place without additional input of energy (i.e., no heating needed). “That’s truly green chemistry,” Lipshutz said. Moreover, the PTS that enables this green chemistry is “benign by design”—it is made from ingredients that are all safe and/or GRAS-affirmed, and thus of no environmental impact. (GRAS is an acronym for Generally Recognized As Safe, an FDA designation.) In fact, Lipshutz says, it’s a pro-vitamin; an ester of vitamin E. “You could drink it.”

The savings in heat needed in many reactions and the waste created by organic solvents could be dramatically reduced using this nanotechnology-based approach. Lipshutz sees this as among his most significant contributions in an already illustrious career as an organic chemist. “If we were to shift just one percent of solvent-based industrial processes to water, that would save 32,000 metric tons (32 million kilos) of organic solvents… and the potential, obviously, is far beyond one percent.”

“We are getting organic solvents out of organic reactions,” he said, “and we’re already looking into next-generation possibilities. All of this green chemistry has come out of developing a way to put CoQ10 and other dietary supplements into water.”

“It’s an opportunity to affect every person on the planet,” he says proudly.

Relevant links: